Thionyl Chloride → Isoxazole, 4-(chloromethyl)-5-methyl-3-phenyl-

HRID 331885노트

반응식

HRID 331885 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13]O.S(Cl)([Cl:17])=O>ClCCl.O>[Cl:17][CH2:13][C:3]1[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][O:6][C:2]=1[CH3:1]

참가 물질

5

반응물 2

HCID 24386Thionyl ChlorideHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

생성물 1

HCID 11052826Isoxazole, 4-(chloromethyl)-5-methyl-3-phenyl-수율 93%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (4.5 g, 236 mmol) in dichloromethane (50 mL) was added at 0° C. thionyl chloride (3.6 g, 2.7 mL, 306 mmol) dropwise over 3 min and the solution stirred at 0° C. for 2 h. After this time, the mixture was diluted with water (50 mL) and the organic phase separated and washed with brine. The aqueous phase was extracted with dichloromethane and the combined extracts dried over sodium sulfate, filtered and evaporated to afford the title compound (4.6 g, 93%) which was obtained as a light brown liquid. MS: m/e=208.1 [M+H]+.

후처리

  1. customthe organic phase separated
  2. washwashed with brine
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined extracts dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-83438939b9a74fa99190bee0be07269c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877782B2

반응 노트

불러오는 중…