Tetrahydrofuran → HCID 67805153, compound

Participants

Reaction Conditions

Reaction Steps

10.0 g. (0.039 mole) of crude acid chloride from Example 5, Step (c), is dissolved in 200 ml. of dry tetrahydrofuran and the solution placed in a 500 ml. round bottom flask fitted with a septum inlet and magnetic stirrer, and held under a nitrogen atmosphere. The solution is cooled to -30° C. in a dry ice/isopropanol bath and 19.5 ml (0.039 mole) of a commercial 2M methyl magnesium bromide solution in dry toluene is added, dropwise, over 30 minutes. After the addition is complete, the mixture is allowed to warm to room temperature and then stirred for 1 hour. The reaction is quenched by the addition of 20 ml. of saturated ammonium chloride solution and the organic layer is separated. The aqueous layer is extracted twice with 20 ml. portions of ether and the combined organic extracts are then dried over anhydrous magnesium sulphate and evaporated to yield the heading compound, m.p. 130° to 133° C., after recrystallization from petroleum ether.

Provenance & Evidence