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

HRID 52166

Reaction equation

HRID 52166 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 19963272N,O-bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamineYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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% ).

Workup

  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

Sources & evidence

ORD record
ord-95e13fad641345f1a3b05938a7cf3c3f
Source dataset
uspto-grants-1997_04
Patent number
US05616596

Linked notes

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