Methanol → 3-(3,5-Difluorophenyl)propan-1-ol

HRID 247416Notes

Reaction equation

HRID 247416 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11](O)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1.CO>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 36694983-(3,5-Difluorophenyl)propionic acid

Product 1

HCID 140499113-(3,5-Difluorophenyl)propan-1-olYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran complex (0.095 mol) was added to a cooled (0°) solution of 3-(3,5-difluorophenyl)propanoic acid (0.043 mol) in tetrahydrofuran (75 ml). The reaction was stirred 2 hours at room temperature, then methanol was carefully added and the reaction was concentrated. The crude product was dissolved in ethyl ether, washed with water, dried over sodium sulfate and concentrated to yield 7 g (95%) of an oily product.

Workup

  1. additionBorane-tetrahydrofuran complex (0.095 mol) was added to
  2. concentrationthe reaction was concentrated
  3. dissolutionThe crude product was dissolved in ethyl ether
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b6d710202a124d13b938d890da0e0c2b
Source dataset
uspto-grants-1987_11
Patent number
US04707488

Reaction notes

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