Triethylamine → (E)-5-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-methylpenta-2,4-dienoic Acid Methyl Ester

HRID 352091노트

반응식

HRID 352091 반응식
[CH3:1][O:2][C:3](=[O:29])[CH:4]=[C:5]([CH3:28])[CH2:6][CH:7]([C:9]1[N:10]([CH:25]([CH3:27])[CH3:26])[C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)C.C(N(CC)CC)C.COC(=O)CC(=O)/C=C/C1N(C(C)C)C2C(C=1C1C=CC(F)=CC=1)=CC=CC=2>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[C:5](\[CH3:28])/[CH:6]=[CH:7][C:9]1[N:10]([CH:25]([CH3:26])[CH3:27])[C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 11326444(E)-5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-oxopent-4-enoic acid methyl esterHCID 698920535-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-methylhex-2-enoic acid methyl ester

생성물 1

HCID 86589178(E)-5-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-methylpenta-2,4-dienoic Acid Methyl Ester

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

2.0 g of crude 5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-methylhex-2-enoic acid methyl ester in 50 ml of toluene are introduced into a 100 ml three-necked round-bottomed flask, equipped with a magnetic stirrer, thermometer, reflux condenser and nitrogen delivery line, 0.9 g (8.87 mmol) of triethylamine are added and the yellow solution is heated at reflux with stirring. After 2 hours, the reaction mixture is cooled, diluted with 50 ml of toluene, washed once with 100 ml of 1N hydrochloric acid and three times with 50 ml of water and concentrated by evaporation using a rotary evaporator. The crude product (orange oil) is purified by means of flash chromatography (hexane/ethyl acetate=10:1). An orange resin is obtained which, according to NMR, contains approximately 30% (E)-5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-oxopent-4-enoic acid methyl ester (mixture of keto and enol forms).

후처리

  1. customequipped with a magnetic stirrer
  2. temperaturethermometer, reflux condenser
  3. temperaturethe yellow solution is heated
  4. temperatureat reflux
  5. temperaturethe reaction mixture is cooled
  6. washwashed once with 100 ml of 1N hydrochloric acid and three times with 50 ml of water
  7. concentrationconcentrated by evaporation
  8. customa rotary evaporator
  9. customThe crude product (orange oil) is purified by means of flash chromatography (hexane/ethyl acetate=10:1)
  10. customAn orange resin is obtained which

출처 및 근거

ORD 기록
ord-f44235eb87ad4baa99fee36a07dfa2f1
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743926B2

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