Phenacyl bromide → Diazoacetophenone

HRID 1397369노트

반응식

HRID 1397369 반응식
C1CCN2C(=NCCC2)CC1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].C1(C)C=CC(S([NH:31][NH:32]S(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1>C1COCC1>[N+:31](=[CH:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15])=[N-:32]

참가 물질

5

반응물 3

HCID 6259Phenacyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 301521N,N'-Bis(p-toluenesulfonyl)hydrazine

생성물 1

HCID 18667Diazoacetophenone수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

DBU (7.5 mL, 50.2 mmol) was added dropwise to a solution of 2-bromo-1-phenylethanone (2.0 g, 10.05 mmol) and N,N′-bis(p-toluenesulfonyl)hydrazine (6.8 g, 20.1 mmol) in dry THF (30 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, and quenched with aqueous saturated NaHCO3 solution. The organic product was extracted with EtOAc and the combined extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 10-15% EtOAc in petroleum ether) to get 2-diazo-1-phenylethanone (1.2 g, yield 82%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.78-7.76 (m, 2H), 7.56-7.53 (m, 1H), 7.48-7.43 (m, 2H), 5.91 (s, 1H).

후처리

  1. customquenched with aqueous saturated NaHCO3 solution
  2. extractionThe organic product was extracted with EtOAc
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluant 10-15% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-32af7f05623242f4ae7b78ac9ed9fd28
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

반응 노트

불러오는 중…