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

HRID 52166

반응식

HRID 52166 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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% ).

후처리

  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

출처 및 근거

ORD 기록
ord-95e13fad641345f1a3b05938a7cf3c3f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616596

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