Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 4-[2-[2-[(2-chloro)-ethoxy]-phenyl]-ethenyl]-1H-indole

HRID 1906192노트

반응식

HRID 1906192 반응식
[NH:1]1[C:9]2[C:4](=[C:5]([CH:10]=[CH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.S(O[CH2:30][CH2:31][Cl:32])(C1C=CC(C)=CC=1)(=O)=O>[OH-].[Na+].O>[Cl:32][CH2:31][CH2:30][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:11]=[CH:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2

참가 물질

5

반응물 2

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 541413862-[(1H-indol-4-yl)-ethenyl]-phenol

생성물 1

HCID 542356984-[2-[2-[(2-chloro)-ethoxy]-phenyl]-ethenyl]-1H-indole수율 39.5%

시약·촉매·용매 2

HCID 962Water용매HCID 14798Sodium Hydroxide용매

실험 절차

4 g of 2-[(1H-indol-4-yl)-ethenyl]-phenol obtained in Step A of Example 1 in 100 ml of 2N sodium hydroxide after having added 6 g of 2-chloroethanol tosylate were heated for 6 hours at reflux and the mixture was left for 16 hours at ambient temperature, then diluted with water and extracted with ethyl acetate. After eliminating the solvent under reduced pressure and chromatography on silica (eluent: benzene), 2 g of 4-[2-[2-[(2-chloro)-ethoxy]-phenyl]-ethenyl]-1H-indole (trans E) were obtained.

후처리

  1. temperaturewere heated for 6 hours
  2. temperatureat reflux
  3. extractionextracted with ethyl acetate

출처 및 근거

ORD 기록
ord-f69f9a797ebb4410b183cea7efe2b7f4
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04650811

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