Triphenylphosphine → 5-(1-azido-2-ethylbutyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole

HRID 2243123ノート

反応式

HRID 2243123 の反応式
[CH2:1]([CH:3]([CH2:21][CH3:22])[CH:4]([C:6]1[N:10]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:9]=[CH:8][CH:7]=1)O)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P([N:68]=[N+:69]=[N-:70])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[N:68]([CH:4]([C:6]1[N:10]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:9]=[CH:8][CH:7]=1)[CH:3]([CH2:21][CH3:22])[CH2:1][CH3:2])=[N+:69]=[N-:70]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 685938962-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butan-1-ol

生成物 1

HCID 866000035-(1-azido-2-ethylbutyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butan-1-ol (0.250 g, 0.778 mmol) in THF (10 mL) at 0° C. was added triphenylphosphine (0.307 g, 1.17 mmol), diethyl azodicarboxylate (0.18 mL, 1.2 mmol), and diphenylphosphoryl azide (0.25 mL, 1.2 mmol). The reaction mixture was warmed to room temperature and stirred for 20 h. The solvent was removed in vacuo and the resulting residue was purified by column chromatography (EtOAc/hexanes, 15:85) to give 0.260 g (97%) of 5-(1-azido-2-ethylbutyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole with an aromatic impurity as judged by 1H NMR. This compound was used in the next step without further purification.

後処理

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was purified by column chromatography (EtOAc/hexanes, 15:85)

出典と根拠

ORDレコード
ord-7a1e7b911969423bb008379880fc4ad4
出典データセット
uspto-grants-2010_03
特許番号
US07674813B2

反応ノート

読み込み中…