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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1789016Generated: October 30, 2026

Cyclopentyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoate → 5-Cyclopentyl 3-methyl 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate

https://huagongshe.com/reaction/1789016

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCyclopentyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoateHCID 54059666—
ReactantMethyl 3-amino-4-fluoro-2-butenoateHCID 73668923—
Solventtert-ButanolHCID 6386—
Product5-Cyclopentyl 3-methyl 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylateHCID 70090527—

Reaction Steps

A solution of the product of step (a) (5.1 g, 14.3 mmoles) and methyl 3-amino-4-fluoro-2-butenoate (1.9 g, 14.3 mmoles) in dry tert-butanol (25 ml) was heated to 60° (oil bath temperature) for 108 hours. The solution was allowed to cool to room temperature and the solvent removed in vacuo. Chromatography on silica eluting with dichloromethane afforded the title compound as a yellow oil which crystallises on addition of petroleum ether (60°-80° ) to afford the title compound 1.5 g mp 148°-9°. (Identical with the product of Example 3).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04686217
Source datasetuspto-grants-1987_08
ORD IDord-a018ff87fe284e27a01f07bd10715329
Source noteuspto-grants-1987_08