Sodium borohydride → 4-Cyclopentylbutan-1-ol

HRID 1071173Notes

Reaction equation

HRID 1071173 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 219320564-Cyclopentylbutanal

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-1300ab512c8a4751bb1502d043ef4969
Source dataset
uspto-grants-2005_06
Patent number
US06903218B2

Reaction notes

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