Sodium borohydride → (1-Phenylcyclopentyl)methanol

HRID 2169151Notes

Reaction equation

HRID 2169151 reaction equation
[C:1]1([C:7]2([CH:12]=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([C:7]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 110951241-Phenylcyclopentane-1-carbaldehyde

Product 1

HCID 123544(1-Phenylcyclopentyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-phenyl-cyclopentanecarbaldehyde 22-01 (23 g, 132.18 mmol) in methanol (300 mL) was added NaBH4 (10.04 g, 264.36 mmol) at 0° C. The mixture was stirred at room temperature for 16 h. After completion of the reaction, it was quenched with aqueous ammonium chloride solution. The mixture was concentrated as much as possible, then diluted with water, extracted with ethyl acetate and the separated organic part was dried over sodium sulfate and concentrated under reduced pressure to get a crude product which was purified using a normal silica column using 5% ethyl acetate in hexane to of ford (1-phenyl-cyclopentyl)-methanol (23-01) (4.5 g, 19.35%) as a yellow liquid.

Workup

  1. customAfter completion of the reaction, it
  2. customwas quenched with aqueous ammonium chloride solution
  3. concentrationThe mixture was concentrated as much as possible,
  4. additionthen diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialthe separated organic part was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-783234d284b94b3ea9207a3f6c6cae58
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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