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US 4,073,799 AGranted
Process for producing 3-formylcyclopentanone derivatives
Assignee(Zaidanhojin) Sagami Chemical Research Center
InventorsKiyoshi Kondo, Daiei Tunemoto, Etsuko Hiro
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Abstract
A novel process for producing 3-formylcyclopentanone derivatives which are useful intermediates for syntheses of five-membered ring compounds such as prostaglandins is disclosed. In the process, 3-formylcyclopentanone derivatives are produced starting from .beta.-dicarbonyl compounds and azides through several-step reactions.
Claims1
A process for producing a 3-formylcyclopentanone derivative having the formula ##STR12## which comprises:
- reacting a .beta.-dicarbonyl compound having the formula ##STR13## with an azide under basic conditions to produce an .alpha.-diazo-.beta.-dicarbonyl compound having the formula ##STR14## treating said product under conditions suitable for producing a carbene or carbenoid to produce a bicyclo hexane-2-one derivative having the formula:
- ##STR15## reacting said product with a mercaptan having the formula, R.sub.5 SH, in the presence of a base to produce a cyclopentanone derivative having the formula ##STR16## reacting said product with an alkylating agent having the formula RZ in the presence of a base to produce a cyclopentanone derivative having the formula ##STR17## decarboxylating said product to produce a cyclopentane sulfide derivative having the formula ##STR18## oxidizing said product to produce a cyclopentanone sulfoxide derivative having the formula ##STR19## reacting said product with an acid anhydride;
- and treating the obtained product with an acid or a base;
- wherein R.sub.4 is an alkyl or an alkoxy group;
- R.sub.5 is a hydrocarbon group having less than 10 carbon atoms;
- R is a C.sub.1-10 alkyl or C.sub.2-10 alkenyl group substituted by a lower alkoxycarbonyl group, X is a hydrogen atom, an alkoxy group, a tetrahydropyranyloxy group or a silyloxy group;
- and Z is a leaving anion.
4 more elements
Dependencies are inferred from the claim text.