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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 569552
Notes
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Reaction equation

HRID 569552 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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
  4. customThe residue was chromatographed over silica gel
  5. washwas eluted with a 1-1 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-d3eef4feb3284db9a51a22c4e9d961c1
Source dataset
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04732903

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes