Process for the preparation of alkynols

Details Process for the preparation of alkynols Process for the preparation of alkynols

2008-05-13

2008-05-13

Eyler, Yvonne (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

Reexamination Certificate

active

07371901

ABSTRACT:
Process for the preparation of an alkynol with formula HC≡C—CH(OH)—R2(formula 2) wherein R2represents methyl, halomethyl or ethyl, wherein the corresponding silyl-protected alkynol ester with formula 1wherein R1represents H, or an optionally substituted alkyl, an optionally substituted alkenyl or an optionally substituted (hetero)aryl group, R2is as defined above and A3Si represents a trisubstituted silyl group wherein each A independently represents an optionally substituted alkyl or an optionally substituted (hetero)aryl group, in the presence of water and at least an equivalent amount of amine functionalities is converted into the alkynol with formula 2. Preferably, the amount of water is between 0.5 and 3 equivalents calculated with respect to the amount of silyl-protected alkynol ester with formula (1).

REFERENCES:
Takano et al, Synthesis of Optically Active 4-Benzyloxymethyl- and 4-(4-Methoxyphenoxy)methyl-buten-2-olids via Lipase-Mediated Resolution, Synthesis, No. 12, Dec. 1993, pp. 1253-1256.
Allevi et al, “Lipase-catalysed resolution of (R)- and (S)-1-trimethylsilyl-1-alkyn-3-ols: useful intermediates for the synthesis of opticallhy active gamma-lactones”, Tetrahedron, Asymmetry, vol. 8, No. 1, Jan. 9, 1997, pp. 93-99.
Gallagher et al, “PMHS-Mediated Couplings of Alkynes or Benzothiazoles with Various Electrophiles: Application to the Synthesis of (−)-Akolactone”, Journal of Organic Chemistry, vol. 68, No. 17, Aug. 22, 2003. pp. 6775-6779.
Thompson et al, “FR901464 Total Synthesis, Proof of Structure, and Evaluation of Synthetic Analogues”, Journal of The American Chemical Society, vol. 123, No. 41, Sep. 25, 2001, pp. 9974-9983.
International Search Report mailed Feb. 9, 2005 in PCT/EP2004/011614.

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