Sodium borohydride → HCID 22261531, compound

HRID 1610673Notes

Reaction equation

HRID 1610673 reaction equation
[CH3:1][C:2]1([CH3:14])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[O:13])[CH2:5][CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH3:14])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:6]([OH:13])[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22261466HCID 22261466, compound

Product 1

HCID 22261531HCID 22261531, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one (5.780 g, 30.70 mmol) in methanol (40 ml) was added sodium borohydride (1.16 g, 30.7 mmol) by small portions under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, diluted with water, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium 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. concentrationThe reaction solution was concentrated under reduced pressure
  3. additiondiluted with water
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-6/1)
  8. customto give the objective substance

Sources & evidence

ORD record
ord-e7509d6a5a7441b3ad86c8b73d0b3921
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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