Hydrochloric Acid → Methyl 4-(2-methylindol-3-yl)-4-oxobutyrate

HRID 1974557Notes

Reaction equation

Cl[C:2]([CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])=[O:3].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:14][C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2.Cl>ClCCl.C(OCC)(=O)C>[CH3:14][C:15]1[NH:16][C:17]2[C:22]([C:23]=1[C:2](=[O:3])[CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of methyl 3-(chloroformyl)propionate (3 ml) and aluminum chloride [6.50 g) in dichloromethane (40 ml) was stirred at 20° C. for 1 hour. A solution of 2-methylindole (3 g) in dichloromethane (20 ml) was added to the mixture at 20° C. and the resulting mixture was stirred at 20° C. for 1 hour. The reaction mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of solvent, the residue was purified by column chromatography on silica gel (100 g) eluting with chloroform and with recrystallization from a mixture of ethyl acetate and hexane to give methyl 4-(2-methylindol-3-yl)-4-oxobutyrate (908 mg) as pale brown crystals.

Workup

stirringthe resulting mixture was stirred at 20° C. for 1 hour
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over magnesium sulfate
customAfter evaporation of solvent
customthe residue was purified by column chromatography on silica gel (100 g)
washeluting with chloroform and with recrystallization from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-631f1cdb54c1487e843046536bee7f79
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05283251

Reaction notes

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