2,2,2-Trifluoroethanol → (S)alpha-cyano-3-phenoxy-4-fluoro-benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylate

HRID 1719779Notes

Reaction equation

HRID 1719779 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[CH3:7][C:8]1([CH3:36])[C@@H:10](/[CH:11]=[CH:12]\[C:13](=[O:15])Cl)[C@H:9]1[C:16]([O:18][C@H:19]([C:34]#[N:35])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:21]=1)=[O:17].P(O)(O)([O-])=O.[Na+]>C(Cl)Cl>[CH3:7][C:8]1([CH3:36])[C@@H:10](/[CH:11]=[CH:12]\[C:13](=[O:15])[O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[C@H:9]1[C:16]([O:18][C@H:19]([C:34]#[N:35])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:21]=1)=[O:17]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 23672064Monosodium phosphateHCID 86740334(S)alpha-cyano-3-phenoxy-4-fluorobenzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-chloro-1-propenyl]-cyclopropane-carboxylate

Product 1

HCID 86740335(S)alpha-cyano-3-phenoxy-4-fluoro-benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 ml of 2,2,2-trifluoroethanol were added at 20° C. to a solution of 2.14 g of the product of Step D in 8 ml of methylene chloride and the mixture was stirred for 90 minutes and was poured into aqueous monosodium phosphate solution. The decanted organic phase was washed with water, dried and evaporated to dryness under reduced pressure The residue was chromatographed over silica gel and was eluted with a 1-1 cyclohexane-ethyl acetate mixture to obtain 2.33 g of (S)α-cyano-3-phenoxy-4-fluoro-benzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylate melting at 56° C. and having a specific rotation of [α]D20 =+42°±1° (c=1% in CHCl3).

Workup

  1. washThe decanted organic phase was washed with water
  2. customdried
  3. customevaporated to dryness under reduced pressure The residue
  4. customwas chromatographed over silica gel
  5. washwas eluted with a 1-1 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-f9dfd289f2b64e7b8272440c2d3093bd
Source dataset
uspto-grants-1985_09
Patent number
US04542142

Reaction notes

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