1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(1-Azidoethyl)-3-phenylbenzofuran

HRID 242855ノート

反応式

HRID 242855 の反応式
C1CCN2C(=NCCC2)CC1.[C:12]1([C:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[O:20][C:19]=2[CH:27](O)[CH3:28])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P([N:44]=[N+:45]=[N-:46])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[N:44]([CH:27]([C:19]1[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:18]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:28])=[N+:45]=[N-:46]

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2 回HCID 199401P,P-Diphenylphosphinic azide2 回HCID 681575611-(3-Phenylbenzofuran-2-yl)ethanol

生成物 1

HCID 866688702-(1-Azidoethyl)-3-phenylbenzofuran収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

DBU (155 μL, 1.04 mmol) was added dropwise to a solution of 1-(3-phenylbenzofuran-2-yl)ethanol (206 mg, 0.864 mmol) and diphenyl phosphoryl azide (255 μL, 1.04 mmol) in anhydrous THF (7 mL) at 0° C. under a nitrogen atmosphere. After 30 min stirring at 0° C., the mixture was slowly warmed to RT and stirring was continued for 1.5 h. Additional diphenyl phosphoryl azide (255 μL, 1.04 mmol) and DBU (155 μL, 1.04 mmol) were added and stirring was continued for 18 h. Volatiles were removed under reduced pressure and the resulting residues was purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane) affording the title compound as an oil (186 mg, 82%). LCMS: RT 4.48 min [M+H-N2]+ 236.1.

後処理

  1. temperaturethe mixture was slowly warmed to RT
  2. stirringstirring
  3. waitwas continued for 1.5 h
  4. stirringstirring
  5. waitwas continued for 18 h
  6. customVolatiles were removed under reduced pressure
  7. customthe resulting residues was purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-91c0c7d28590456785fcb0ae8d56314d
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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