Sodium borohydride → 4-Hydroxy-decanoic Acid 3,7-dimethyl-oct-6-enyl Ester

HRID 1018163Notes

Reaction equation

HRID 1018163 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]([CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH2:5][CH2:6][O:7][C:8](=[O:19])[CH2:9][CH2:10][C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>O.C1COCC1.CCOCC>[CH3:3][CH:4]([CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH2:5][CH2:6][O:7][C:8](=[O:19])[CH2:9][CH2:10][CH:11]([OH:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 538305424-Oxo-decanoic Acid 3,7-dimethyl-oct-6-enyl Ester

Product 1

HCID 542824114-Hydroxy-decanoic Acid 3,7-dimethyl-oct-6-enyl Ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.0 g sodium borohydride in 30 ml of water was cooled to 5° C. A solution of 4-oxo-decanoic acid 3,7-dimethyl-oct-6-enyl ester in 75 ml of THF was added to the reaction during 12 minutes and the resulting reaction mixture was stirred at room temperature for 5 hours. Then the reaction mixture was diluted with ether, washed with saturated NaHCO3, brine and water. The organic phase was dried, filtered and evaporated to dryness. The resulting liquid was purified by chromatography to yield 7.6 g of a liquid.

Workup

  1. customthe resulting reaction mixture
  2. washwashed with saturated NaHCO3, brine and water
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe resulting liquid was purified by chromatography

Sources & evidence

ORD record
ord-79b7928aad4c4bcabe10a5e659af6234
Source dataset
uspto-grants-2002_11
Patent number
US06479682B1

Reaction notes

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