Sodium borohydride → (1-Phenylcyclopentyl)methanol

HRID 1409552Notes

Reaction equation

HRID 1409552 reaction equation
[BH4-].[Na+].[C:3]1([C:9]2([CH:14]=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[C:3]1([C:9]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 110951241-Phenylcyclopentane-1-carbaldehyde

Product 1

HCID 123544(1-Phenylcyclopentyl)methanolYield 79.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (3.2 g, 86.2 mmol) was added portion wise to a cooled (ice bath) solution of 1-phenyl-cyclopentanecarbaldehyde (7.5 g, 43.1 mmol) in methanol (100 ml) and then stirred for 16 h at RT. After completion of the reaction, it was quenched with saturated ammonium chloride solution and the methanol under reduced pressure. The mixture was diluted with water, extracted with EtOAc, washed with water, brine, dried (Na2SO4) and evaporated to dryness under reduced pressure. Chromatography (15% EtOAc in hexanes) provided (1-phenyl-cyclopentyl)-methanol as a white solid (6 g, 79.8%).

Workup

  1. customAfter completion of the reaction, it
  2. customwas quenched with saturated ammonium chloride solution
  3. additionThe mixture was diluted with water
  4. extractionextracted with EtOAc
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-091ce8b74e79417386d1143d35765396
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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