Sodium borohydride → 5-Methyl-3-phenylhexan-2-ol

HRID 1446403Notes

Reaction equation

HRID 1446403 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5](=[O:7])[CH3:6].[BH4-].[Na+]>CO>[CH3:1][CH:2]([CH3:14])[CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:5]([OH:7])[CH3:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131565125-Methyl-3-phenylhexan-2-one

Product 1

HCID 222704255-Methyl-3-phenylhexan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 66 mg (0.345 mmol) of 5-methyl-3-phenyl-2-hexanone in 1 mL MeOH was treated with 16 mg sodium borohydride. After 1.5 h, the reaction was quenched with 1.2 N HCl and concentrated. The residue was partitioned between EtOAc and water. The organic layer was washed with brine, dried and concentrated to yield the crude title compound which was used without purification. 1H NMR: (500 MHz, CDCl3): δ 0.88 (2d, 6H), 1.0-1.8 (m, 4H), 1.2 (d, 3H), 2.64 (m, 1H), 3.9 (m, 1H), 7.2-7.4 (m, 5H).

Workup

  1. customthe reaction was quenched with 1.2 N HCl
  2. concentrationconcentrated
  3. customThe residue was partitioned between EtOAc and water
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-accfadecf8e942e5a1525fdd9979419f
Source dataset
uspto-grants-2010_02
Patent number
US07667053B2

Reaction notes

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