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

HRID 242884ノート

反応式

HRID 242884 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 82.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

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, 0.86 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 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 continued for 18 h. The volatiles were removed in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane) affording the title compound as an oil (186 mg, 82%). LCMS (Method C): RT 4.48 min [M+H-N2]+ 236.1

後処理

  1. waitwas continued for 1.5 h
  2. stirringstirring
  3. waitcontinued for 18 h
  4. customThe volatiles were removed in vacuo
  5. customthe resulting residue purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-f9ae375694fc425cb2550c11b491dd0c
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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