tert-Butanol → (S)alpha-cyano-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-[(Z) 3-chloro-3-oxo-1-propenyl]-cyclopropane carboxylate

HRID 569538Notes

Reaction equation

[Cl:1]C(N(C)C)=C(C)C.C(O)(C)(C)C.[CH3:14][C:15]1([CH3:42])[C@@H:17](/[CH:18]=[CH:19]\[C:20](=O)[OH:21])[C@H:16]1[C:23]([O:25][C@H:26]([C:40]#[N:41])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:28]=1)=[O:24]>C(Cl)Cl>[CH3:14][C:15]1([CH3:42])[C@@H:17](/[CH:18]=[CH:19]\[C:20](=[O:21])[Cl:1])[C@H:16]1[C:23]([O:25][C@H:26]([C:40]#[N:41])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:28]=1)=[O:24]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 0.25 ml of 1-chloro-N,N,2-trimethylpropenylamine, 7.5 ml of methylene chloride and 1.5 ml of tert.-butanol was added to a solution of 0.5 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propenyl]-cyclopropane-carboxylate in 7.5 ml of methylene chloride and the mixture was stirred at 20° C. for 48 hours. The mixture was extracted with methylene chloride and the organic phase was washed with water and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-2 hexane-ether mixture to obtain 0.43 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-chloro-1-propenyl]-cyclopropane-carboxylate melting at 86° C.

Workup

extractionThe mixture was extracted with methylene chloride
washthe organic phase was washed with water
customevaporated to dryness under reduced pressure
customThe residue was chromatographed over silica gel
washwas eluted with an 8-2 hexane-ether mixture

Sources & evidence

ORD record: ord-e14cecd295a245dfb567c54c92e40b1a
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04732903

Reaction notes

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