Acetaldehyde → O-benzyl-N-vinyl-hydroxylamine

HRID 530066Notes

Reaction equation

HRID 530066 reaction equation
[CH:1](=O)[CH3:2].Cl.[CH2:5]([O:12][NH2:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O.CO>[CH2:5]([O:12][NH:13][CH:1]=[CH2:2])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 177AcetaldehydeHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 57227192O-benzyl-N-vinyl-hydroxylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Acetaldehyde (24.7 mL, 44.2 mmol) was added dropwise to the cooled solution (0° C.) of O-benzyl-hydroxylamine hydrochloride (7.00 g, 43.85 mmol) in water (100 mL) and MeOH (20 mL). The reaction mixture was stirred for 16 h. The volatiles were removed under reduced pressure, and the water suspension was extracted with EtOAc (2×75 mL). The combined organic extracts were washed with brine, and then dried over Na2SO4 and evaporated to yield O-benzyl-N-vinyl-hydroxylamine (LXVI) in quantitative yield. 400 MHz 1H NMR (DMSO-d6, ppm) 7.48 (0.5H, q, J=5.8 Hz), 7.39-7.26 (5H, m), 6.86 (0.5H, q, J=5.5 Hz), 5.06 (1H, s), 4.97 (1H, s), 1.78 (1.5H, d, J=5.5 Hz), 1.76 (1.5H, d, J=5.8 Hz).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. extractionthe water suspension was extracted with EtOAc (2×75 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-8607523e4386483db0ed92a546e0931e
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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