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

HRID 242884노트

반응식

HRID 242884 반응식
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]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2회HCID 199401P,P-Diphenylphosphinic azide2회HCID 681575611-(3-Phenylbenzofuran-2-yl)ethanol

생성물 1

HCID 866688702-(1-Azidoethyl)-3-phenylbenzofuran수율 82.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-f9ae375694fc425cb2550c11b491dd0c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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