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

HRID 242855노트

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HRID 242855 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%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-91c0c7d28590456785fcb0ae8d56314d
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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