Sodium borohydride → 4-Cyclopentylbutan-1-ol

HRID 1004645Notes

Reaction equation

HRID 1004645 reaction equation
[CH:1]1([CH2:6][CH2:7][CH2:8][CH:9]=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[CH:1]1([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 219320565732-95-6

Product 1

HCID 217976434-Cyclopentylbutan-1-olYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Cyclopentyl-butyraldehyde (4.9 g, 35 mmol) was taken up in ethanol (100 mL) and treated slowly with sodium borohydride (1.72 g, 4.54 mmol). The reaction was stirred for three days and quenched with water (10 mL). The reaction was diluted with dichloromethane (200 mL) and washed with water (2×100 mL). The organic phase was dried (MgSO4), filtered, and concentrated to yield an oil. The product was passed through a pad of silica to yield 4-cyclopentyl-butan-1-ol as a colorless oil (3.12 g, 63%).

Workup

  1. customquenched with water (10 mL)
  2. additionThe reaction was diluted with dichloromethane (200 mL)
  3. washwashed with water (2×100 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield an oil

Sources & evidence

ORD record
ord-1612288e8b024818bf4af09b0642a0cc
Source dataset
uspto-grants-2000_04
Patent number
US06051586

Reaction notes

Loading…