Triphenylphosphine → N,O-bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamine

HRID 52166

Reaktionsgleichung

Reaktionsgleichung von HRID 52166
[CH3:1][CH:2](O)[C:3]#[CH:4].[O:6]([C:13]([NH:15][O:16][C:17]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18])=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:6]([C:13]([N:15]([CH:3]([C:2]#[CH:1])[CH3:4])[O:16][C:17]([O:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:18])=[O:14])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 162393-Butyn-2-olHCID 5462977Diethyl azodicarboxylateHCID 10107329N,O-Bis-(phenoxycarbonyl)-hydroxylamine

Produkt 1

HCID 19963272N,O-bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamineAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 0° C. solution in THF (200 mL) of 3-butyn-2-ol (3.00 g, 42.9 mmol), N,O-bis(phenoxycarbonyl)hydroxylamine (11.7 g, 42.9 mmol), and triphenylphosphine (11.7 g, 42.9 mmol), was added dropwise diethylazodicarboxylate (7.40 g, 42.8 mmol). The reaction mixture was stirred for 2 hours at 0°-5° C. and then was concentrated almost to dryness. The residue was diluted with ethyl acetate, the solids were filtered off, and the flitrate was concentrated in vacuo. Chromatography on silica gel (5% ethyl acetate, pentane) provided N,O-bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamine (12.3 g, 88% ).

Aufarbeitung

  1. concentrationwas concentrated almost to dryness
  2. additionThe residue was diluted with ethyl acetate
  3. filtrationthe solids were filtered off
  4. concentrationthe flitrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-95e13fad641345f1a3b05938a7cf3c3f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616596

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