Ethyl 4,4-difluoroacetoacetate → 145374-00-1

HRID 1500894Notes

Reaction equation

HRID 1500894 reaction equation
[F:1][CH:2]([F:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[BH4-].[Na+]>C1(C)C=CC=CC=1>[F:1][CH:2]([F:11])[CH:3]([OH:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 67697Ethyl 4,4-difluoroacetoacetateHCID 4311764Sodium borohydride

Product 1

HCID 14383477145374-00-1Yield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a cooled solution of ethyl 4,4-difluoro-3-oxobutanoate (5.0 g, 30.1 mmol) in toluene (150 mL) was added NaBH4 (1.26 g, 33.1 mmol) at 0° C. The mixture was then stirred at RT for 4.5 hours. The reaction was quenched with aqueous HCl (10%) carefully. The separated aqueous phase was extracted with EtOAc (20 mL×2). The combined organic phases were dried over Na2SO4, and then filtered and then concentrated in vacuo to give the crude ethyl 4,4-difluoro-3-hydroxybutanoate as colorless oil (3.8 g, yield: 76%).

Workup

  1. customThe reaction was quenched with aqueous HCl (10%) carefully
  2. extractionThe separated aqueous phase was extracted with EtOAc (20 mL×2)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-97ca5058bc67413a9c80f207c9d18b94
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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