Hydrochloric Acid → 2-(5-Ethyl-1H-indol-3-ylmethyl)-malonic acid diethyl ester

HRID 384856노트

반응식

HRID 384856 반응식
[CH3:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:9][CH:10]=[C:11]([CH2:12]N(C)C)[C:5]=2[CH:4]=1.[C:16]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[Na].Cl>>[CH2:21]([O:20][C:18](=[O:19])[CH:17]([CH2:12][C:11]1[C:5]2[C:6](=[CH:7][CH:8]=[C:3]([CH2:2][CH3:1])[CH:4]=2)[NH:9][CH:10]=1)[C:16]([O:24][CH2:25][CH3:26])=[O:23])[CH3:22]

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 2696951H-Indole-3-methanamine, 5-ethyl-N,N-dimethyl-HCID 5360545Sodium

생성물 1

HCID 588430642-(5-Ethyl-1H-indol-3-ylmethyl)-malonic acid diethyl ester수율 85.1%

반응 조건

온도
120 °C

실험 절차

The 5-Ethylgramine (1.25 g, 6.18 mmol) was combined with diethyl malonate (2.85 mL, 18.54 mmol) and heated to 120° C. until a homogeneous solution was formed. To this mixture was added sodium metal (100 mg, 4.36 mmol) and the mixture was stirred at 120° C. for 24 hours. TLC indicated the completion of the reaction. The reaction was allowed to cool to room temperature and a solution of 5% HCl (aqueous) was slowly added to the mixture and the resulting product was extracted with EtOAc. The organic layer was washed with saturated sodium bicarbonate, dried over anhydrous magnesium sulafate, filtered and evaporated to give compound 12 as a white solid (1.67 g; 85% yield; M+1=318.4). The product was taken into the next step without purification.

후처리

  1. customwas formed
  2. customthe completion of the reaction
  3. temperatureto cool to room temperature
  4. extractionthe resulting product was extracted with EtOAc
  5. washThe organic layer was washed with saturated sodium bicarbonate
  6. dry with materialdried over anhydrous magnesium sulafate
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-836277ff9aa04819b175d2caf566e8b3
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367828B2

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