Acetaldehyde → O-benzyl-N-vinyl-hydroxylamine

HRID 1752130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1752130
[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

Komponenten

5

Edukt 2

HCID 177AcetaldehydeHCID 102312Benzyloxyamine hydrochloride

Produkt 1

HCID 57227192O-benzyl-N-vinyl-hydroxylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c4352ac75c404dd5acae3a350dd23f81
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09162992B2

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