Sodium borohydride → HCID 22261565, compound

HRID 1610259Notes

Reaction equation

HRID 1610259 reaction equation
[CH3:1][CH:2]1[CH2:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[C:3]1=[O:13].[BH4-].[Na+]>CO>[CH3:1][CH:2]1[CH2:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[CH:3]1[OH:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11073910HCID 11073910, compound

Product 1

HCID 22261565HCID 22261565, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-methyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one (24.93 g, 143.1 mmol) in methanol (150 ml) was added sodium borohydride (5.41 g, 143 mmol) by small portions under ice-cooling and the mixture was stirred at room temperature for 1 hr. The solvent of the reaction solution was evaporated under reduced pressure, water was added, and the mixture was extracted twice with ethyl acetate. The collected 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=2/1) to give the objective substance.

Workup

  1. temperaturecooling
  2. customThe solvent of the reaction solution was evaporated under reduced pressure, water
  3. additionwas added
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. dry with materialThe collected 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=2/1)
  8. customto give the objective substance

Sources & evidence

ORD record
ord-3ec538a7a3ac4a04b60b112ce9c3d985
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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