Phosphorus oxychloride → 3-(chloromethyl)-1-tosyl-1H-indole

HRID 41535

반응식

HRID 41535 반응식
[S:1]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20]O)=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].O=P(Cl)(Cl)[Cl:24]>C1COCC1>[Cl:24][CH2:20][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]([S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH:12]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 839263(1-tosyl-1H-indol-3-yl)methanol

생성물 1

HCID 668519953-(chloromethyl)-1-tosyl-1H-indole수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (1-tosyl-1H-indol-3-yl)methanol (1.0 g, 3.318 mmol) in dry THF (10 mL), POCl3 (0.661 g, 4.314 mmol) was added at 0° C. and the mixture was stirred for 10 min. The reaction mixture was allowed to warm to ambient temperature and refluxed for 3 h. The solvent was removed under reduced pressure at 45° C. and the crude reaction mixture was quenched with saturated NaHCO3 solution and extracted with DCM. The organic layer was separated and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield the title compound as a solid (1.04 g, 98%).

후처리

  1. temperaturerefluxed for 3 h
  2. customThe solvent was removed under reduced pressure at 45° C.
  3. customthe crude reaction mixture
  4. customwas quenched with saturated NaHCO3 solution
  5. extractionextracted with DCM
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e45db4d755b9499d802a03d699de345d
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530648B2

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