5,5-Diethoxy-(Z3)-3-Pentenyl Methoxymethyl Ether and...

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

Reexamination Certificate

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Reexamination Certificate

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07834220

ABSTRACT:
Provided is a method for preparing (E3,Z5)-3,5-alkadienyl acetate and (E3,Z5)-3,5-dodecadienyl acetate which is a sex pheromone of Brazilian apple leafminer. Specifically, provided is a method for preparing (E3,Z5)-3,5-alkadienyl acetate, comprising steps of hydrolyzing 5,5-diethoxy-(Z3)-3-pentenyl methoxymethyl ether in the presence of an acid to obtain 4-formyl-(E3)-butenyl methoxymethyl ether; reacting the 4-formyl-(E3)-butenyl methoxymethyl ether with alkylidene triphenylphosphorane in accordance with the Wittig reaction to obtain (E3,Z5)-3,5-alkadienyl methoxymethyl ether; and obtaining (E3,Z5)-3,5-alkadienyl acetate using the (E3,Z5)-3,5-alkadienyl methoxymethyl ether as a starting substance.

REFERENCES:
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patent: 63-039837 (1998-02-01), None
patent: 2007-070276 (2007-03-01), None
patent: 2007-161676 (2007-06-01), None
patent: WO 01/36368 (2001-05-01), None
Unelius et al., Identification and Synthesis of the Sex Pheromone ofPhtheochroa cranaodes(Lepidoptera: Tortricidae),Tetrahedron Letter, vol. 37, No. 9, pp. 1505-1508 (1996).
Coracini et al., Behavioural effects of minor sex pheromone components in Brazilian apple leafrollerBonagota cranaodes(Lep., Tortricidae),J. Appl. Ent., 127, pp. 427-434 (2003).
Kocienski, “Protecting Groups”, Foundations of Organic Chemistry Series, pp. 22-29, 82-85.
Jhillu Singh Yadav; Etukala Jagan Reddy; Synthesis of (3E, 5Z)-3,5-Dodecadienylacetate, the Sex Pheromone ofPhtheochroa cranaodes(Lepidoptera: Tortricidae); Japanese Society for Bioscience, Biotechnology and Biochecmistry; vol. 64; pp. 1726-1728; 2000.
Valentine Ragoussis; Maria Panopoulou; Nikitas Ragoussis; Concise Preparation of the (3E,5Z)- Alkadienyl System. New Approach to the Synthesis of Principal Insect Sex Pheromone Constituents; Journal of Agricultural and Food Chemistry; vol. 52; pp. 5047-5051; 2004.
Official Action mailed Mar. 2, 2010, and issued in connection with corresponding Japanese Patent Application No. 2007-309892 dated Feb. 25, 2010.

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