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

HRID 1193598Notes

Reaction equation

HRID 1193598 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-965730c0ef0e4b98bebc1656a9a14426
Source dataset
uspto-grants-1989_03
Patent number
US04810811

Reaction notes

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