Methyl 2,2-difluoro-2-phenylacetate → 2,2-Difluoro-2-phenylethanol

HRID 911568Notes

Reaction equation

HRID 911568 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:19])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9](OC)=[O:10]>C1COCC1>[F:7][C:8]([F:19])([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 12585535Methyl 2,2-difluoro-2-phenylacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 97938912,2-Difluoro-2-phenylethanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add lithium aluminum hydride (5.18 mL, 5.18 mmol, 1M solution in THF) to a solution of methyl difluorophenylethanoate (0.964 g, 5.18 mmol, prepared by following the procedure described in J. Org. Chem. 1995, 60, 5174-5179) in anhydrous THF (10 mL) at 0° C. Stir the mixture at room temperature for 45 min. Cool to 0° C. and quench with EtOAc and then water. Separate the organic phase and extract twice the aqueous phase with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to provide the desired intermediate (0.8 g, 98%) that was used without any further purification.

Workup

  1. customprepared
  2. customat 0° C
  3. temperatureCool to 0° C.
  4. customquench with EtOAc
  5. customSeparate the organic phase
  6. extractionextract twice the aqueous phase with EtOAc
  7. dry with materialDry the combined organic extracts over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f6d0dd1d7ca34a509adc7d80b412bcc7
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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