Hydrochloric Acid → 2-(5-Ethyl-1H-indol-3-ylmethyl)-malonic acid diethyl ester
Reaction equation
[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]Participants
Conditions
- Temperature
- 120 °C
Procedure
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.
Workup
- customwas formed
- customthe completion of the reaction
- temperatureto cool to room temperature
- extractionthe resulting product was extracted with EtOAc
- washThe organic layer was washed with saturated sodium bicarbonate
- dry with materialdried over anhydrous magnesium sulafate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-a556edf0d70c4537b7d7fdea2d623f88
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348338B2
Reaction notes
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