Toluene → HCID 53997352, compound

Participants

Reaction Conditions

Reaction Steps

3-methylfuran-2-carboxaldehyde imine (1.5 g, 8.15 mmol), methyl acrylate (3.5 g, 40.7 mmol) and diisopropyl ethyl amine (2.1 g, 16.3 mmol) were mixed in toluene (6 ml) and stirred at 80° C. Ethyl chloroformate (1.77 g, 16.3 mmol) was added to the mixture. After completing the addition, the reaction mixture was heated for one hour under reflux and allowed to cool to room temperature. Water was added and the mixture was extracted with toluene. The organic layer was washed with an aqueous solution of sodium chloride and dried over sodium sulfate. The solvent was distilled off to obtain crude products of N-ethoxycarbonyl-N-phenyl-7-amino-4,5,6,7-tetrahydrobenzo[b]furan-6-carboxylic acid methyl ester. Silica gel column chromatography using a developing solvent of hexane/ethyl acetate=5/1, gave a fraction containing the desired product, which was concentrated by distilling off the solvent, to obtain 1.2 g (yield: 43.0% from imine) of N-ethoxycarbonyl-N-phenyl-7-amino-4,5,6,7tetrahydrobenzo[b]furan-6-carboxylic acid methyl ester. 1H-NMR spectra (chemical shift, ppm: in CDCl3): 1.00-1.40 (3H, m), 1.65-2.10 (2H, m), 2.15-3.05 (joined 2H, m), 3.74 (3H, s), 3.95-4.30 (3H, m), 5.75-6.20 (joined 1H, m), 6.50-6.95 (2H, m), 7.00-7.50 (5H, m).

Provenance & Evidence