Sodium borohydride → 1-(4-Bromophenyl)butan-2-ol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:12])[CH2:10][CH3:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([OH:12])[CH2:10][CH3:11])=[CH:6][CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 70B (478 mg, 2.1 mmol) in 5 mL MeOH at 0° C., was added NaBH4 (110 mg, 2.98 mmol). The solution was stirred at rt for 30 min, then was diluted with EtOAc and washed with H2O and brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-30% EtOAc/hexanes) afforded 70C (460 mg, 96%). MS (ESI) m/z 221.2 (M-OH)+.
Workup
- washwashed with H2O and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customPurification via flash chromatography (0-30% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-d4fa01af1dda438c93d87216ef8a2f6e
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592331B2
Reaction notes
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