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

HRID 384856ノート

反応式

HRID 384856 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-836277ff9aa04819b175d2caf566e8b3
出典データセット
uspto-grants-2013_02
特許番号
US08367828B2

反応ノート

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