Ethyl Acetate → (R)-2-(4-bromophenyl)propan-1-ol

HRID 735698Notes

Reaction equation

HRID 735698 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH3:12])[C:9](O)=[O:10])=[CH:4][CH:3]=1.CCOC(C)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([CH3:12])[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 12953949(R)-2-(4-bromophenyl)propanoic acid

Product 1

HCID 54290945(R)-2-(4-bromophenyl)propan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 76C (95 mg, 0.42 mmol) in THF (3 mL) at 0° C., was added BH3 (1M in THF, 0.4 mL, 4 mmol). The mixture was stirred rt for 16 h. EtOAc (20 mL) was added, and the organic phase washed with 1M H3PO4, sat. NaHCO3 and brine, dried (Na2SO4), and concentrated to give 76D (90 mg, 100%). MS (ESI) m/z 197.0 (M−H2O+H)+.

Workup

  1. washthe organic phase washed with 1M H3PO4, sat. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a9617d23127c494ebba9c3869d79d6b0
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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