Methanol → HCID 14348494, compound

HRID 654985Notes

Reaction equation

HRID 654985 reaction equation
[BH4-].[Na+].CO.[O:5]=[C:6]([CH:21]([CH3:31])[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:7][C:8]([O:10][CH2:11]C1C=CC([N+]([O-])=O)=CC=1)=[O:9]>C(OCC)(=O)C>[O:5]=[C:6]([CH:21]([CH3:31])[CH2:22][O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 14348493HCID 14348493, compound

Product 1

HCID 14348494HCID 14348494, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (1.89 g; 50 mmole) was added to methanol (20 ml), and the solution was heated under reflux for 10 minutes and then allowed to cool to room temperature. p-Nitrobenzyl 3-oxo-5-benzyloxy-4-methylpentanoate (3.7 g; 10 mmole) was dropwise added thereto, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with dilute hydrochloric acid and an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography to give methyl 3-oxo-5-benzyloxy-4-methylpentanoate.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 10 minutes
  3. washwashed with dilute hydrochloric acid
  4. dry with materialan aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  5. customAfter removal of the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-53735b8952464b7da801cd01849481ff
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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