Ethoxalyl chloride → Ethyl 6-chloro-2-(ethoxycarbonyl)-1-methyl-oxo-1h-indole-3-acetate

HRID 1280398Notes

Reaction equation

Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:16]2[CH3:19])=[CH:12][CH:11]=1>ClCCCl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]([C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:16]2[CH3:19])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 7.1 ml (63.6 mmol) of ethyl chlorooxoacetate in 100 ml of 1,2-dichloroethane is cooled to 0° C. 7.0 ml (63.6 mmol) of titanium tetrachloride are added in small portions and the mixture is stirred for 30 min at 0° C. A solution of 7.4 g (35.3 mmol) of ethyl 6-chloro-1-methyl-1H-indole-2-carboxylate is added and the mixture is stirred for 3 h at room temperature. The mixture is poured onto water and the organic phase is separated by settling, washed with dilute sodium hydroxide solution, dried over sodium sulphate and concentrated under reduced pressure to produce an oil which is purified by chromatography on a silica column (eluant: cyclohexane/dichloromethane: 2/8). 9.51 g (29.4 mmol) of compound are isolated in the form of a white solid.

Workup

stirringthe mixture is stirred for 3 h at room temperature
additionThe mixture is poured onto water
customthe organic phase is separated
washwashed with dilute sodium hydroxide solution
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure
customto produce an oil which
customis purified by chromatography on a silica column (eluant: cyclohexane/dichloromethane: 2/8)

Sources & evidence

ORD record: ord-2c3a0a28ddcc45349c3a2a6e37a2d362
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451795B1

Reaction notes

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