(4S)-Hydroxy-3-methyl-2-(2-propenyl)-2-cyclopentene-1-one → HCID 86739809, compound

HRID 1154408Notes

Reaction equation

HRID 1154408 reaction equation
[CH3:1][C:2]1([CH3:15])[C@@H:4](/[CH:5]=[C:6](\[Cl:11])/[C:7](=[O:10])[O:8][CH3:9])[C@H:3]1[C:12](Cl)=[O:13].[OH:16][C@H:17]1[CH2:21][C:20](=[O:22])[C:19]([CH2:23][CH:24]=[CH2:25])=[C:18]1[CH3:26]>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:15])[C@@H:4](/[CH:5]=[C:6](\[Cl:11])/[C:7](=[O:10])[O:8][CH3:9])[C@H:3]1[C:12]([O:16][CH:17]1[CH2:21][C:20](=[O:22])[C:19]([CH2:23][CH:24]=[CH2:25])=[C:18]1[CH3:26])=[O:13]

Participants

4

Reactant 2

HCID 12225760(4S)-Hydroxy-3-methyl-2-(2-propenyl)-2-cyclopentene-1-oneHCID 131714066HCID 131714066, compound

Product 1

HCID 86739809HCID 86739809, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(1R,cis) 2,2-dimethyl-3(Z)-[2-chloro-3-oxo-3-methoxy-propenyl]-cyclopropane-1-carboxylic acid chloride and (4S)-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one were reacted to obtain (S) 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl (1R,cis) 2,2-dimethyl-3(Z)-[2-chloro-3-oxo-3-methoxy-propenyl]-cyclopropane-1-carboxylate with a specific rotation of [α]D20 =-15°±4° (c=0.25% in benzene)

Sources & evidence

ORD record
ord-bf853c14dace4f27908e2712f77d1d76
Source dataset
uspto-grants-1984_12
Patent number
US04489093

Reaction notes

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