Acetaldehyde → O-benzyl-N-vinyl-hydroxylamine

HRID 1752130ノート

反応式

HRID 1752130 の反応式
[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

参加物

5

反応物 2

HCID 177AcetaldehydeHCID 102312Benzyloxyamine hydrochloride

生成物 1

HCID 57227192O-benzyl-N-vinyl-hydroxylamine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c4352ac75c404dd5acae3a350dd23f81
出典データセット
uspto-grants-2015_10
特許番号
US09162992B2

反応ノート

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