Pyridine → 3'-Fluoro-4'-methoxyacetophenone-o-3-fluorobenzyloxime

HRID 41958

반응식

HRID 41958 반응식
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([F:12])[CH:5]=1)=O.Cl.[F:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][O:19][NH2:20].N1C=CC=CC=1>C(O)C>[F:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][O:19][N:20]=[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([F:12])[CH:5]=1)[CH3:1]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 968281-(3-Fluoro-4-methoxyphenyl)ethan-1-oneHCID 23206139o-(3-Fluorobenzyl)hydroxylamine hydrochloride

생성물 1

HCID 871386653'-Fluoro-4'-methoxyacetophenone-o-3-fluorobenzyloxime수율 90.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 3-fluoro-4-methoxyacetophenone (0.063 g, 0.377 mmol), O-(3-fluorobenzyl)hydroxylamine hydrochloride (0.100 g, 0.569 mmol) and pyridine (0.14 ml, 1.73 mmol) in ethanol (5 ml) was stirred at reflux under nitrogen for 4 h and cooled to room temperature. The solution was concentrated to a pale yellow oil which was diluted with water. The suspension was extracted with dichloromethane (×3). The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated to a white solid. The crude product was purified by column chromatography (SiO2), eluting with 95:5 petrol/ethyl acetate, to give 3′-fluoro-4′-methoxyacetophenone-O-3-fluorobenzyloxime (CP9-126) as a white solid (0.099 g, 90%), m.p. 67°.

후처리

  1. temperatureat reflux under nitrogen for 4 h
  2. concentrationThe solution was concentrated to a pale yellow oil which
  3. additionwas diluted with water
  4. extractionThe suspension was extracted with dichloromethane (×3)
  5. washThe combined organic phases were washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to a white solid
  9. customThe crude product was purified by column chromatography (SiO2)
  10. washeluting with 95:5 petrol/ethyl acetate

출처 및 근거

ORD 기록
ord-5b90820628314994913bf3c02418e6c9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536157B2

연결된 노트

불러오는 중…