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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1942537Generated: October 31, 2026

Methanol → Methyl 1-(4-methoxybutyl)-3,3-dimethyl-2-oxoindoline-6-carboxylate

https://huagongshe.com/reaction/1942537

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantDimethylformamideHCID 6228—
ReactantTriethylamineHCID 8471—
ReactantTriphenylphosphineHCID 11776—
Reactant6-Bromo-1-(4-methoxybutyl)-3,3-dimethyl-1,3-dihydro-2H-indol-2-oneHCID 58376234—
Catalystpalladium(II) acetateHCID 167845—
SolventWaterHCID 962—
ProductMethyl 1-(4-methoxybutyl)-3,3-dimethyl-2-oxoindoline-6-carboxylateHCID 67330620—

Reaction Conditions

Temperature100 °C

Reaction Steps

To 6-bromo-1-(4-methoxybutyl)-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (1.0 g) were added palladium acetate (207 mg), triphenylphosphine (484 mg), triethylamine (0.86 ml), methanol (0.62 ml), and DMF (10 ml), and the mixture was stirred at 100° C. under carbon monoxide atmosphere for 4 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate solution. This ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give the title compound (480 mg) as a pale yellow liquid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08389511B2
Source datasetuspto-grants-2013_03
ORD IDord-d9dd2799b6cc48d89fc6374b975df357
Source noteuspto-grants-2013_03