Water → HCID 18433867, compound

HRID 2305954Notes

Reaction equation

HRID 2305954 reaction equation
[BH4-].[Na+].[CH:3]1([CH2:8][CH2:9][CH2:10][C:11](=[O:13])[CH3:12])[CH2:7][CH2:6][CH2:5][CH2:4]1.O>CO>[CH:3]1([CH2:8][CH2:9][CH2:10][CH:11]([OH:13])[CH3:12])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 18433881HCID 18433881, compound

Product 1

HCID 18433867HCID 18433867, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

NaBH4 (3.15 g; 83 mmol) was added portionwise to a solution of 5-cyclopentylpentan-2-one (16.0 g; 104 mmol) in MeOH (125 ml) at 0° C. The mixture was stirred at 0° C. for 1 hour then at room temperature for 2 hours. Water (100 ml) was added cautiously and the mixture extracted with MTBE (3×250 ml). The organic phases were combined, washed with brine (3×50 ml), dried over MgSO4, concentrated in vacuo and distilled (52° C.-56° C./0.045 torr) to give 14.5 g (90% yield) of 5-cyclopentylpentan-2-ol.

Workup

  1. waitat room temperature for 2 hours
  2. extractionthe mixture extracted with MTBE (3×250 ml)
  3. washwashed with brine (3×50 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. distillationdistilled (52° C.-56° C./0.045 torr)

Sources & evidence

ORD record
ord-3e8c26c723b548749a9f094c530e40b3
Source dataset
uspto-grants-2002_08
Patent number
US06441052B1

Reaction notes

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