Water → HCID 15589467, compound

HRID 1383196Notes

Reaction equation

HRID 1383196 reaction equation
[CH3:1][C:2]1([CH3:32])[C@@H:4](/[CH:5]=[C:6](/[F:12])\[C:7](=[O:11])[O:8]CC)[C@H:3]1[C:13]([O:15][C@H:16]([C:30]#[N:31])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:18]=1)=[O:14].O1CCOCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH3:1][C:2]1([CH3:32])[C@@H:4](/[CH:5]=[C:6](/[F:12])\[C:7](=[O:8])[OH:11])[C@H:3]1[C:13]([O:15][C@H:16]([C:30]#[N:31])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:18]=1)=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 312751,4-DioxaneHCID 13041483HCID 13041483, compound

Product 1

HCID 15589467HCID 15589467, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.5 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3(E)-[2-fluoro-3-oxo-3-ethoxy-propenyl]-cyclopropane-1-carboxylate, 10 ml of dioxane, 2.5 ml of water and 1 g of p-toluene sulfonic acid manohydrate was refluxed for 24 hours and then allowed to cool to room temperature. Methylene chloride was added to the mixture and the 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 60-40-1 cyclohexane-ethyl acetate-acetic acid mixture to obtain 980 mg of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3(E)-[2-fluoro-3-oxo-3-hydroxy-propenyl]-cyclopropane-1-carboxylate.

Workup

  1. washthe 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 60-40-1 cyclohexane-ethyl acetate-acetic acid mixture

Sources & evidence

ORD record
ord-ea69a48e511b46f3bd1965fb29f3f95f
Source dataset
uspto-grants-1989_02
Patent number
US04808749

Reaction notes

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