Sodium borohydride → HCID 22272611, compound

HRID 1064861Notes

Reaction equation

HRID 1064861 reaction equation
[NH2:1][C:2]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH:13]([CH3:15])[CH3:14].[BH4-].[Na+]>ClCCl.CO.O>[NH2:1][C:2]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 22272615HCID 22272615, compound

Product 1

HCID 22272611HCID 22272611, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixed solution of this aldehyde (745 mg, 3.63 mmol) in dichloromethane (5 ml) and methanol (10 ml) was added sodium borohydride (280 mg, 7.40 mmol) with ice-cooling and stirred at room temperature for 1 hour. The reaction solution was diluted with water and extracted with chloroform. The organic layer was washed with a saturated sodium hydrochloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (silica gel 50 g, developing solvent; hexane:ethyl acetate=6:1 2:1) to provide 736 mg (yield 98%) of 4-amino-3,5-diisopropylbenzenemethanol as colorless oil.

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with a saturated sodium hydrochloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by a silica gel column chromatography (silica gel 50 g, developing solvent; hexane:ethyl acetate=6:1 2:1)

Sources & evidence

ORD record
ord-6a7d859b8c1e48b395c89f27c20faed5
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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