Water → 5-allyloxy-1-benzenesulfonyl-1H-indole

HRID 854505노트

반응식

HRID 854505 반응식
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)[CH:4]=[CH2:5].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C1COCC1>[CH2:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([S:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:24])=[O:23])[CH:11]=[CH:10]2)[CH:4]=[CH2:5]

참가 물질

6

반응물 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 142392305-(prop-2-en-1-yloxy)-1H-indole

생성물 1

HCID 685493765-allyloxy-1-benzenesulfonyl-1H-indole수율 48.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a slurry of 0.45 g (9.4 mmol) sodium hydride (50% dispersion in mineral oil) in 40 mL anhydrous THF was added 1.90 g 5-allyloxyindole. The slurry was stirred at room temperature for 15 min upon which time 1.14 mL (9 mmol) benzene sulfonyl chloride was added dropwise. The reaction was stirred at room temperature over three nights and then poured into water and extracted with ethyl acetate. The organic extracts were dried over MgSO4 and concentrated. The product solidified upon concentration and the crude material was triturated with diethyl ether to afford 1.36 g of 5-allyloxy-1-benzenesulfonyl-1H-indole as a light brown solid.

후처리

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. concentrationThe product solidified upon concentration
  6. customthe crude material was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-839bbe3a334e439aaf2dcf107072c64d
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259182B2

반응 노트

불러오는 중…