Indole → 1-(2-chloroethyl)-1H-indole

HRID 2228368노트

반응식

HRID 2228368 반응식
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[Cl:12][CH2:13][CH2:14]OS(C1C=CC(C)=CC=1)(=O)=O>O1CCCC1>[Cl:12][CH2:13][CH2:14][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

참가 물질

5

반응물 3

HCID 798IndoleHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 24758Sodium hydride

생성물 1

HCID 108992601-(2-chloroethyl)-1H-indole수율 40.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Into a flask of 500 ml capacity fitted with a stirrer and cooling tube, there were introduced 7.2 g (corresponding to 0.21 mol) of an oil dispersion of NaH and 50 ml of tetrahydrofuran, and the mixture was stirred on an ice-water bath. Into this mixture there was added dropwise, little by little, a solution in which 24.60 g (0.21 mol) of indole were dissolved in 100 ml of tetrahydrofuran. After completion of the dropwise addition, the ice-water bath was removed and the mixture was stirred for one hour at room temperature. Then, 49.29 g (0.21 mol) of 2-chloroethyl-p-toluene sulfonate were added, and the reaction performed under heated reflux whilst stirring for 15 hours. After completion of the reaction, the undissolved material was removed by filtration, and concentration was performed under reduced pressure. This reaction mixture was purified by column chromatography using silica gel, to obtain 15.4 g of 1-(2-chloroethyl)indole.

후처리

  1. customInto a flask of 500 ml capacity fitted with a stirrer
  2. temperaturecooling tube
  3. additionInto this mixture there was added dropwise
  4. additionAfter completion of the dropwise addition
  5. customthe ice-water bath was removed
  6. stirringthe mixture was stirred for one hour at room temperature
  7. temperatureunder heated
  8. temperaturereflux
  9. stirringwhilst stirring for 15 hours
  10. customAfter completion of the reaction
  11. customthe undissolved material was removed by filtration, and concentration
  12. customThis reaction mixture was purified by column chromatography

출처 및 근거

ORD 기록
ord-4d92950e24ef448e9dca9402ceaf3ef3
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06416939B1

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