2-Azido-1-phenylethanone → Diazoacetophenone

HRID 541010노트

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HRID 541010 반응식
[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])=[N+:2]=[N-].C1(P(C2C=CC=CC=2)CCC(ON2C(=O)CCC2=O)=O)C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)Cl>[N+:1](=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])=[N-:2]

참가 물질

5

반응물 2

HCID 109865532-Azido-1-phenylethanoneHCID 426043111-((3-(Diphenylphosphanyl)propanoyl)oxy)pyrrolidine-2,5-dione

생성물 1

HCID 18667Diazoacetophenone수율 49.2%

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

A solution of azide 2i (74 mg, 0.459 mmol) in anhydrous toluene (1.5 mL) was cooled to 0° C. A solution of phosphine 1e (171 mg, 0.482 mmol) in toluene (1.0 mL) was added dropwise. The resulting solution was maintained at 0° C. for 2 h and was then allowed to warm to room temperature. The mixture was then diluted with anhydrous CH2Cl2 (5 mL) and was stirred for an additional 30 min. The solution was then placed directly on a column of silica gel and eluted with 15% EtOAc/hexanes to give diazo-compound 5i as a yellow oil (33 mg, 0.226 mmol, 49% yield).

후처리

  1. temperatureto warm to room temperature
  2. washeluted with 15% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-eba32a62c9d945f28f85eb12f78448b3
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871916B2

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