Sodium borohydride → HCID 54185237, compound

HRID 1975634Notes

Reaction equation

HRID 1975634 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]([CH:8]=[CH:9][CH:10]1[CH2:14][CH2:13][CH:12]([CH3:15])[C:11]1([CH3:17])[CH3:16])[C:5](=[O:7])[CH3:6]>C(O)C>[CH3:3][CH:4]([CH:8]=[CH:9][CH:10]1[CH2:14][CH2:13][CH:12]([CH3:15])[C:11]1([CH3:17])[CH3:16])[CH:5]([OH:7])[CH3:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57091011HCID 57091011, compound

Product 1

HCID 54185237HCID 54185237, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 0.58 g of NaBH4 (18 mmoles) in 50 ml of ethanol cooled to 0° C. are added drop by drop within one hour 5 g (24 mmoles) of 3-methyl-5-(2,2,3-trimethyl-cyclopent-1-yl)-pent-4-en-2-one. The reaction mixture is stirred for 90 minutes at room temperature. The ethanol is removed by rotary evaporation and the reaction mass is extracted with ether and washed with water. After evaporation of the solvent the crude product is vacuum distilled, to yield 3-methyl-5-(2,2,3-trimethyl-cyclopent-1-yl)-pent-4-en-2-ol: 4.4 g (mixture of isomers)

Workup

  1. customThe ethanol is removed by rotary evaporation
  2. extractionthe reaction mass is extracted with ether
  3. washwashed with water
  4. customAfter evaporation of the solvent the crude product
  5. distillationdistilled

Sources & evidence

ORD record
ord-353640d8ac9b458db0751cb9e3dcf7f2
Source dataset
uspto-grants-1994_02
Patent number
US05288701

Reaction notes

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