Thionyl Chloride → (1R,3S)-3-(Cyclopentylidenemethyl)-2,2-dimethylcyclopropane-1-carbonyl chloride

HRID 2198395Notes

Reaction equation

HRID 2198395 reaction equation
[CH3:1][C:2]1([CH3:14])[C@@H:4]([CH:5]=[C:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[C@H:3]1[C:11](O)=[O:12].S(Cl)([Cl:17])=O>>[CH3:1][C:2]1([CH3:14])[C@@H:4]([CH:5]=[C:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[C@H:3]1[C:11]([Cl:17])=[O:12]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 11106237(1R,cis) 2,2-dimethyl-3-(cyclopentylidenemethyl)-cyclopropane-carboxylic acid

Product 1

HCID 45082002(1R,3S)-3-(Cyclopentylidenemethyl)-2,2-dimethylcyclopropane-1-carbonyl chloride

Procedure

A mixture of (1R,cis) 2,2-dimethyl-3-(cyclopentylidenemethyl)-cyclopropane-carboxylic acid and thionyl chloride in petroleum ether (b.p.=40° to 70° C.) was refluxed to obtain (1R,cis) 2,2-dimethyl-3-(cyclopentylidenemethyl)-cyclopropane-carboxylic acid chloride which was then reacted with R,S α-hydroxy-6-phenoxy-2-pyridine-acetonitrile in benzene in the presence of pyridine to obtain (R,S)α-cyano-(6-phenoxy-2-pyridyl)-methyl (1R,cis) 2,2-dimethyl-3-(cyclopentylidenemethyl)-cyclopropane-carboxylate.

Workup

  1. temperaturewas refluxed

Sources & evidence

ORD record
ord-6643abcac2314ef7be6706e0d28db373
Source dataset
uspto-grants-1982_11
Patent number
US04357335

Reaction notes

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