Benzene → HCID 12507637, compound

Participants

Reaction Steps

To a solution consisting of 3-acetyldihydro-2(3H)-furanone (25.6 g, 0.2 mole), tryptophol (32.2 g, 0.2 mole) and benzene (700 ml), p-toluenesulfonic acid (0.50 g) is added. The flask is equipped with a water separator and a condenser. The mixture is stirred at reflux for one hr. More p-toluenesulfonic acid (0.50 g) is added and the solution is refluxed for 18 hr. The dark solution is cooled and stirred in presence of silica gel (100 g) for 5 min. The mixture is filtered on diatomaceous earth and charcoal. The silica gel is washed with diethyl ether (2×100 ml) and the filtrates are evaporated to afford an oil which is a mixture of two diasteroisomers of the title compound. If desired, the latter oil can be crystallizated from methanol to obtain crystals (17 g) of isomer A of the title compound, mp 162°-164° C. The mother liquor of this crystallization is evaporated to obtain a residue (20 g) containing mainly isomer B of the title compound.

Provenance & Evidence