Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2000-06-12
2003-07-15
Richter, Johann (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S174000, C560S178000
Reexamination Certificate
active
06593488
ABSTRACT:
TECHNICAL FIELD
The present Invention relates to novel 4-fluoro-3-oxocarboxylates which are important as synthetic intermediates of aminopyrimidine derivatives (Japanese Provisional Patent Publications No. 230036/1993, No. 25187/1994, No. 116247/1994, No. 247939/1994, and No. 258223/1995) useful as an insecticide, acaricide, fungicide or nematocide, and the process for producing the same.
BACKGROUND ART
The 4-fluoro-3-oxocarboxylates of the present invention are novel compounds.
An object of the present invention is to provide a process for industrially producing 4-fluoro-3-oxocarboxylates which are novel compounds and important as synthetic intermediates of aminopyrimidine derivatives (Japanese Provisional Patent Publications No. 230036/1993, No. 25187/1994, No. 116247/1994, No. 247939/1994 and No. 258223/1995) useful as an insecticide, acaricide, fungicide or nematocide with a low cost and good yield.
The present inventors have studied to solve the above-mentioned problem, and as a result, they have found that 4-fluoro-3-oxocarboxylates which are novel compounds become an important synthetic intermediate for the above-mentioned useful aminopyrimidine derivatives, and established the preparation process to accomplish the present invention.
DISCLOSURE OF THE INVENTION
That is, the first invention relates to a 4-fluoro-3-oxocarboxylate represented by the following formula (1):
wherein R
1
represents an alkyl group or an aryl group;
R
2
and R
3
each represent a hydrogen atom or an alkyl group;
and R
4
represents an alkyl group.
The second invention relates to a process for preparing a 4-fluoro-3-oxocarboxylate represented by the above formula 1), which comprises allowing a 2-fluorocarboxylate represented by the following formula (2):
wherein R
1
and R
2
have the same meanings as defined above;
and R
5
represents an alkyl group, to react with a carboxylate represented by the following formula (3):
wherein R
3
and R
4
have the same meanings as defined above, in the presence of a base.
BEST MODE FOR CARRYING OUT THE INVENTION
In the following, the present invention is explained in detail.
R
1
to R
5
in the 4-fluoro-3-oxocarboxylate (Compound (1)) which is an objective compound and in the starting materials for the preparation thereof (the compound (2) represented by the formula (2), and the compound (3) represented by the formula (3)) are as mentioned below.
As R
1
, there may be mentioned an alkyl group and an aryl group.
As the alkyl group of R
1
, there may be mentioned a straight or branched alkyl group having 1 to 10 carbon atoms; preferably 1 to 4 carbon atoms, more preferably a methyl group, an ethyl group, an n-propyl group and an n-butyl group.
As the aryl group of R
1
, there may be mentioned an aryl group having 6 to 10 carbon atoms; preferably a phenyl group.
As R
2
and R
3
, there may be mentioned a hydrogen atom and an alkyl group.
As the alkyl group of R
2
and R
3
, there may be mentioned a straight or branched alkyl group having 1 to 10 carbon atoms; preferably 1 to 4 carbon atoms. As R
2
, a straight alkyl group having 1 to 4 carbon atoms is preferred, and particularly preferred is a methyl group. As R
3
, a straight alkyl group having 1 to 4 carbon atoms is preferred, and particularly preferred is a methyl group.
As R
4
and R
5
, there may be mentioned an alkyl group.
As the alkyl group of R
4
and R
5
, there may be mentioned a straight or branched alkyl group having 1 to 10 carbon atoms; preferably 1 to 4 carbon atoms. As R
4
, a methyl group, an ethyl group or an n-butyl group is more preferred. As R
5
, a methyl group, an ethyl group or an n-butyl group is more preferred.
The compound (1) of the present invention is exemplified below. There may be mentioned
methyl 4-fluoro-3-oxopentanoate,
methyl 4-fluoro-3-oxohexanoate,
methyl 4-fluoro-3-oxoheptanoate,
methyl 4-fluoro-3-oxooctanoate,
methyl 4-fluoro-2-methyl-3-oxopentanoate,
methyl 4-fluoro-2-methyl-3-oxohexanoate,
methyl 4-fluoro-2-methyl-3-oxoheptanoate,
methyl 4-fluoro-2-methyl-3-oxooctanoate,
methyl 4-fluoro-4-methyl-3-oxopentanoate,
methyl 4-fluoro-4-methyl-3-oxohexanoate,
methyl 4-fluoro-4-methyl-3-oxoheptanoate,
methyl 4-fluoro-4-methyl-3-oxooctanoate,
methyl 4-fluoro-2,4-dimethyl-3-oxopentanoate,
methyl 4-fluoro-3-oxo-4-phenylbutanoate,
methyl 4-fluoro-2-methyl-3-oxo-4-phenylbutanoate,
ethyl 4-fluoro-3-oxopentanoate,
ethyl 4-fluoro-3-oxohexanoate,
ethyl 4-fluoro-3-oxoheptanoate,
ethyl 4-fluoro-3-oxooctanoate,
ethyl 4-fluoro-2-methyl-3-oxopentanoate,
ethyl 4-fluoro-2-methyl-3-oxohexanoate,
ethyl 4-fluoro-2-methyl-3-oxoheptanoate,
ethyl 4-fluoro-2-methyl-3-oxooctanoate,
ethyl 4-fluoro-4-methyl-3-oxopentanoate,
ethyl 4-fluoro-4-methyl-3-oxohexanoate,
ethyl 4-fluoro-4-methyl-3-oxoheptanoate,
ethyl 4-fluoro-4-methyl-3-oxooctanoate,
ethyl 4-fluoro-2,4-dimethyl-3-oxopentanoate,
ethyl 4-fluoro-3-oxo-4-phenylbutanoate,
ethyl 4-fluoro-2-methyl-3-oxo-4-phenylbutanoate,
propyl 4-fluoro-3-oxopentanoate,
propyl 4-fluoro-3-oxohexanoate,
propyl 4-fluoro-3-oxoheptanoate,
propyl 4-fluoro-3-oxooctanoate,
propyl 4-fluoro-2-methyl-3-oxopentanoate,
propyl 4-fluoro-2-methyl-3-oxohexanoate,
propyl 4-fluoro-2-methyl-3-oxoheptanoate,
propyl 4-fluoro-2-methyl-3-oxooctanoate,
propyl 4-fluoro-4-methyl-3-oxopentanoate,
propyl 4-fluoro-2,4-dimethyl-3-oxopentanoate,
propyl 4-fluoro-3-oxo-4-phenylbutanoate,
propyl 4-fluoro-2-methyl-3-oxo-4-phenylbutanoate,
butyl 4-fluoro-3-oxopentanoate,
butyl 4-fluoro-3-oxohexanoate,
butyl 4-fluoro-3-oxoheptanoate,
butyl 4-fluoro-3-oxooctanoate,
butyl 4-fluoro-2-methyl-3-oxopentanoate,
butyl 4-fluoro-2-methyl-3-oxohexanoate,
butyl 4-fluoro-2-methyl-3-oxoheptanoate,
butyl 4-fluoro-2-methyl-3-oxooctanoate,
butyl 4-fluoro-4-methyl-3-oxopentanoate,
butyl 4-fluoro-2,4-dimethyl-3-oxopentanoate,
butyl 4-fluoro-3-oxo-4-phenylbutanoate,
butyl 4-fluoro-2-methyl-3-oxo-4-phenylbutanoate,
isopropyl 4-fluoro-3-oxopentanoate,
isopropyl 4-fluoro-3-oxohexanoate,
isopropyl 4-fluoro-3-oxoheptanoate,
isopropyl 4-fluoro-3-oxooctanoate,
isopropyl 4-fluoro-2-methyl-3-oxopentanoate,
isopropyl 4-fluoro-2-methyl-3-oxohexanoate,
isopropyl 4-fluoro-2-methyl-3-oxoheptanoate,
isopropyl 4-fluoro-2-methyl-3-oxooctanoate,
isopropyl 4-fluoro-4-methyl-3-oxopentanoate,
isopropyl 4-fluoro-2,4-dimethyl-3-oxopentanoate,
isopropyl 4-fluoro-3-oxo-4-phenylbutanoate,
isopropyl 4-fluoro-2-methyl-3-oxo-4-phenylbutanoate,
isobutyl 4-fluoro-3-oxopentanoate,
isobutyl 4-fluoro-3-oxohexanoate,
isobutyl 4-fluoro-3-oxoheptanoate,
isobutyl 4-fluoro-3-oxooctanoate,
isobutyl 4-fluoro-2-methyl-3-oxopentanoate,
isobutyl 4-fluoro-2-methyl-3-oxohexanoate,
isobutyl 4-fluoro-2-methyl-3-oxoheptanoate,
isobutyl 4-fluoro-2-methyl-3-oxooctanoate,
isobutyl 4-fluoro-4-methyl-3-oxopentanoate,
isobutyl 4-fluoro-2,4-dimethyl-3-oxopentanoate,
isobutyl 4-fluoro-3-oxo-4-phenylbutanoate, and
isobutyl 4-fluoro-2-methyl-3-oxo-4-phenylbutanoate.
Among the compounds as mentioned above, preferred as the compound (1) are exemplified below. They are
methyl 4-fluoro-3-oxopentanoate,
methyl 4-fluoro-3-oxohexanoate,
methyl 4-fluoro-3-oxoheptanoate,
methyl 4-fluoro-3-oxooctanoate,
methyl 4-fluoro-2-methyl-3-oxopentanoate,
methyl 4-fluoro-2-methyl-3-oxohexanoate,
methyl 4-fluoro-2-methyl-3-oxoheptanoate,
methyl 4-fluoro-2-methyl-3-oxooctanoate,
methyl 4-fluoro-4-methyl-3-oxooctanoate,
methyl 4-fluoro-2,4-dimethyl-3-oxopentanoate,
methyl 4-fluoro-3-oxo-4-phenylbutanoate,
methyl 4-fluoro-2-methyl-3-oxo-4-phenylbutanoate,
ethyl 4-fluoro-3-oxopentanoate,
ethyl 4-fluoro-3-oxohexanoate,
ethyl 4-fluoro-3-oxoheptanoate,
ethyl 4-fluoro-3-oxooctanoate,
ethyl 4-fluoro-2-methyl-3-oxopentanoate,
ethyl 4-fluoro-2-methyl-3-oxohexanoate,
ethyl 4-fluoro-2-methyl-3-oxoheptanoate,
ethyl 4-fluoro-2-methyl-3-oxooctanoate,
ethyl 4-fluoro-4-methyl-3-oxopentanoate,
ethyl 4-fluoro-2,4-dimethyl-3-oxopentanoate,
ethyl 4-fluoro-3-oxo-4-phenylbutanoate,
ethyl 4-fluoro-2-methyl-3-oxo-4-phenylbutanoate,
butyl 4-fluoro-3-oxopentanoate,
butyl 4-fluoro-3-oxohexanoate,
butyl 4-fluoro-3-oxoheptanoate, and
butyl 4-fluoro-3-oxooctanoate.
The compound (2) (2-fluorocarboxylate) to be used can be easily ob
Fuse Kensaku
Morita Kazuhiro
Ohmori Kiyoshi
Onduka Yoshitaka
Yokota Naoyuki
Birch & Stewart Kolasch & Birch, LLP
Richter Johann
UBE Industries Ltd.
Zucker Paul A.
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