Sodium borohydride → (E)-N,N-Diethyl-4-hydroxy-2-pentenamide

HRID 1637722Notes

Reaction equation

HRID 1637722 reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4](=[O:10])/[CH:5]=[CH:6]/[C:7](=[O:9])[CH3:8])[CH3:2].[BH4-].[Na+]>CO>[CH2:11]([N:3]([CH2:1][CH3:2])[C:4](=[O:10])/[CH:5]=[CH:6]/[CH:7]([OH:9])[CH3:8])[CH3:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18799723(E)-N,N-Diethyl-4-oxo-2-pentenamide

Product 1

HCID 18799855(E)-N,N-Diethyl-4-hydroxy-2-pentenamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (E)-N,N-diethyl-4-oxo-2-pentenamide (0.73 g, 4.31 mmol) in methanol (10 ml) cooled to 0° C. is added sodium borohydride (0.18 g, 4.75 mmol) under nitrogen stirred for minutes, quenched with excess water, and extracted with ethyl acetate (3×50 ml). The organic extracts are combined, washed with saline (50 ml), dried over sodium sulfate, concentrated in vacuo to give the title compound, NMR (CDCl3) 6.89, 6.42, 4.49, 3.41, 2.51, 1.33, 1.17.

Workup

  1. customquenched with excess water
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washwashed with saline (50 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-128979d304664eeaa39e6bf4cacb299c
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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