Water → 5-(Benzyloxy)pentan-2-ol

HRID 1919767Notes

Reaction equation

HRID 1919767 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][CH2:13][C:14](=[O:16])[CH3:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>CO>[CH2:3]([O:10][CH2:11][CH2:12][CH2:13][CH:14]([OH:16])[CH3:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2812685-(Benzyloxy)pentan-2-oneHCID 4311764Sodium borohydride

Product 1

HCID 117455305-(Benzyloxy)pentan-2-olYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (236 mg) was added to a mixed solution of 5-benzyloxy-2-pentanone (1.09 g, 5.67 mmol) in methanol (50 mL) in an ice bath, followed by stirring. After completion of the reaction, water was added to the reaction solution in an ice bath, and methanol was evaporated. The pH was adjusted to 4 with 2 mol/L hydrochloric acid. After extraction with chloroform-water, the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 957 mg of the title compound (yield: 87%) as a colorless solid.

Workup

  1. additionwas added to the reaction solution in an ice bath
  2. custommethanol was evaporated
  3. extractionAfter extraction with chloroform-water
  4. washthe organic layer was washed with a saturated sodium chloride solution
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a61e331aa5f746b4a845dd4e8aea818d
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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