Sodium borohydride → HCID 57446332, compound

HRID 1610687Notes

Reaction equation

HRID 1610687 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[BH4-].[Na+]>C(O)C.O>[OH:17][CH:10](/[CH:9]=[CH:8]/[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 202607254-Pentenoic acid, 5-(2-methylphenyl)-3-oxo-, eth

Product 1

HCID 57446332HCID 57446332, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl (E)-5-(2-methylphenyl)-3-oxo-4-pentenoate (37.24 g, 160.3 mmol) in ethanol (100 ml) was added sodium borohydride (3.03 g, 80.2 mmol) by small portions under ice-cooling, and the mixture was stirred as it was for 10 min. The reaction solution was diluted with water, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give a crude product of ethyl (E)-3-hydroxy-5-(2-methylphenyl)penta-4-enoate as a yellow liquid.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe recovered organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b9dcd96d39394dacb809a63cfb4f3fda
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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