Water → Ethyl 2-benzyl-3-hydroxybutyrate

HRID 898498Notes

Reaction equation

HRID 898498 reaction equation
[BH4-].[Na+].[OH-].[Na+].O.[CH2:6]([CH:13]([C:19](=[O:21])[CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CO>[CH2:6]([CH:13]([CH:19]([OH:21])[CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 246929Ethyl alpha-benzylacetoacetateHCID 4311764Sodium borohydride

Product 1

HCID 13299637Ethyl 2-benzyl-3-hydroxybutyrateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.05 Mol of NaBH4 and 0.4 g of NaOH were added into 25 ml of water. While cooling the reactor in ice bath, a mixture of 0.07 mol of ethyl 2-benzyl-3-oxo-butyrate and 30 ml of methanol was added dropwise with stirring, and the reaction was stirred at room temperature for 5 hours. After removing the solvent, the product was extracted with ethyl acetate, and the extract was dried over anhydrous Na2SO4. Removing the solvent gave a colorless liquid of 0.06 mol. Yield 85%.

Workup

  1. temperatureWhile cooling the reactor in ice bath
  2. additionwas added dropwise
  3. stirringthe reaction was stirred at room temperature for 5 hours
  4. customAfter removing the solvent
  5. extractionthe product was extracted with ethyl acetate
  6. dry with materialthe extract was dried over anhydrous Na2SO4
  7. customRemoving the solvent
  8. customgave a colorless liquid of 0.06 mol

Sources & evidence

ORD record
ord-3118753faaa64ad49848254dfbdd4f1f
Source dataset
uspto-grants-2008_04
Patent number
US07351778B2

Reaction notes

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