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

HRID 1719763Notes

Reaction equation

HRID 1719763 reaction equation
[CH3:1][C:2]1([CH3:29])[C@@H:4](/[CH:5]=[CH:6]\[C:7](Cl)=[O:8])[C@H:3]1[C:10]([O:12][C@H:13]([C:27]#[N:28])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)=[O:11].[F:30][C:31]([F:38])([F:37])[C:32]([CH3:36])([OH:35])[CH2:33][CH3:34]>C(Cl)Cl>[CH3:1][C:2]1([CH3:29])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:8])[O:35][C:32]([C:31]([F:38])([F:37])[F:30])([CH3:36])[CH2:33][CH3:34])[C@H:3]1[C:10]([O:12][C@H:13]([C:27]#[N:28])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)=[O:11]

Participants

4

Reactant 2

HCID 13335684(S)alpha-cyano-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-[(Z) 3-chloro-3-oxo-1-propenyl]-cyclopropane carboxylateHCID 19838866HCID 19838866, compound

Product 1

HCID 86740325(S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-(1-trifluoromethyl-1-methylpropyloxy)-1-propenyl]-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

900 mg of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-chloro-3-oxo-1-propenyl]-cyclopropane carboxylate were dissolved in 3 ml of methylene chloride and 1 ml of 1-trifluoromethyl-1-methyl propanol was added thereto. The mixture was stirred for 16 hours at room temperature under inert atmosphere and away from humidity. After 3 days at room temperature, the reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate, then with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and eluted with a 8-2 mixture of hexane-ethyl ether to obtain 570 mg of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-(1-trifluoromethyl-1-methylpropyloxy)-1-propenyl]-cyclopropane-carboxylate.

Workup

  1. waitAfter 3 days at room temperature
  2. washthe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materialwith water, dried
  4. customevaporated to dryness
  5. customThe residue was chromatographed over silica gel
  6. washeluted with a 8-2 mixture of hexane-ethyl ether

Sources & evidence

ORD record
ord-4dfae0a444f9415f933d5095e19705e2
Source dataset
uspto-grants-1985_09
Patent number
US04542142

Reaction notes

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