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

HRID 52166

反応式

HRID 52166 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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% ).

後処理

  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

出典と根拠

ORDレコード
ord-95e13fad641345f1a3b05938a7cf3c3f
出典データセット
uspto-grants-1997_04
特許番号
US05616596

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