Water → HCID 21835802, compound

HRID 1741428Notes

Reaction equation

HRID 1741428 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13](=[O:35])[C:14]([F:34])([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:22]=3)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.O>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH:13]([OH:35])[C:14]([F:34])([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:22]=3)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 11812658HCID 11812658, compound

Product 1

HCID 21835802HCID 21835802, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (20 mg, 0.53 mmol) is added to a solution of ethyl 1-(p-chlorophenyl)-α-fluoro-β-oxo-α-(m-phenoxybenzyl)cyclopropanepropionate (214 mg, 0.46 mmol) in methanol at 0° C. The reaction mixture is stirred at 0° C. for 20 minutes, treated with water (2 mL), and concentrated in vacuo to obtain a residue. A solution of the residue in ethyl acetate is washed sequentially with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a colorless gum (224 mg, 100%) which is found to have a 9:1 [R,S and S,R] to [R,R and S,S] ratio by NMR spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customto obtain a residue
  3. washA solution of the residue in ethyl acetate is washed sequentially with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76e187ee8d244d4cbd25f8a127a71579
Source dataset
uspto-grants-1999_10
Patent number
US05973190

Reaction notes

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