Sodium borohydride → HCID 21745198, compound

HRID 37632Notes

Reaction equation

HRID 37632 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH2:15][CH:16]=[O:17])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])[CH3:3].[BH4-].[Na+]>C(O)C.O>[CH3:14][C:11]([C:9]1[CH:8]=[C:7]([CH2:15][CH2:16][OH:17])[CH:6]=[C:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[CH:10]=1)([CH3:12])[CH3:13]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 135421773,5-Bis(1,1-dimethylethyl)benzeneacetaldehyde

Product 1

HCID 21745198HCID 21745198, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the title product of Example 18 (500 mg, 2.14 mmoles) in ethanol (10 ml) is added a solution of sodium borohydride (80.8 mg, 2.14 mmoles) in water (1 ml). After disappearance of starting material as judged by TLC, excess reagent is destroyed by addition of acetic acid, and the mixture concentrated. The residue is partitioned between diethyl ether and water, the organic layer dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using mixtures of ethyl acetate and hexane as eluents affords the title compound.

Workup

  1. customis destroyed by addition of acetic acid
  2. concentrationthe mixture concentrated
  3. customThe residue is partitioned between diethyl ether and water
  4. dry with materialthe organic layer dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e473c0797d39496f8d94da0e81b3b545
Source dataset
uspto-grants-1995_05
Patent number
US05420343

Reaction notes

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