Sodium borohydride → HCID 22262160, compound

HRID 1610658Notes

Reaction equation

HRID 1610658 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5](=[O:13])[CH2:4][CH2:3]1.[BH4-].[Na+]>CO.O>[CH3:1][C:2]1([CH3:14])[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH:5]([OH:13])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 222621376,7,8,9-Tetrahydro-8,8-dimethyl-5H-benzocyclohepten-5-one

Product 1

HCID 22262160HCID 22262160, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 8,8-dimethyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one (29.20 g, 155.1 mmol) in methanol (150 ml) was added sodium borohydride (5.87 g, 155 mmol) by small portions under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction solution was diluted with water and extracted twice with ethyl acetate. The recovered organic layer was-dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-6/1) to give the objective substance.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe recovered organic layer was-dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-6/1)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-6f54df7b6d734435a89cffe844db04ee
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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