Sodium borohydride → (E)-N,N-Diethyl-4-hydroxy-2-pentenamide
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
Product 1
Reagents, catalysts & solvents 1
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
- customquenched with excess water
- extractionextracted with ethyl acetate (3×50 ml)
- washwashed with saline (50 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-128979d304664eeaa39e6bf4cacb299c
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06043248
Reaction notes
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