Sodium borohydride → Methyl 2-(1-hydroxyethyl)-5-phenylpentanoate

HRID 1368292Notes

Reaction equation

HRID 1368292 reaction equation
[C:1]([CH:4]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([CH:4]([CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11333780Methyl 2-acetyl-5-phenylpentanoate

Product 1

HCID 18519827Methyl 2-(1-hydroxyethyl)-5-phenylpentanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.50 g (23.5 mmol) of methyl 2-acetyl-5-phenylpentanoate are introduced into 100 ml of methanol and the mixture is ice-cooled. 0.44 g (11.7 mmol) of sodium borohydride is added in portions and the mixture is stirred for a further 1 h. The solvent is then evacuated from the batch, and the residue is taken up in diethyl ether and washed with 1 N hydrochloric acid. The organic phase is then concentrated again and flash-chromatographed using the eluent petroleum ether/ethyl acetate 10/1.

Workup

  1. temperaturecooled
  2. customThe solvent is then evacuated from the batch
  3. washwashed with 1 N hydrochloric acid
  4. concentrationThe organic phase is then concentrated again
  5. customflash-chromatographed

Sources & evidence

ORD record
ord-2ff033c8156647dc842df3d6c4ba32f2
Source dataset
uspto-grants-2003_06
Patent number
US06573263B2

Reaction notes

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