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

HRID 2304951Notes

Reaction equation

HRID 2304951 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-86f7d65dbbd84865967c249710419434
Source dataset
uspto-grants-2002_08
Patent number
US06437150B1

Reaction notes

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