Ammonium Chloride → HCID 86670260, compound

Participants

Reaction Conditions

Reaction Steps

In a dehydrated tetrahydrofuran (35 ml) solution of N-(4-chloro-phenyl)-thioacetamide (3.3 g), 27 ml of n-butyllithium (1.59 mol/l, n-hexane solution) was added dropwise at 0° C. under a nitrogen atmosphere. After stirring at 0° C. for 1 hour, the mixture was cooled to −78° C. A tetrahydrofuran (35 ml) solution of 5-bromo-2-methyl-2-pentene (2.9 g) was added dropwise thereto. After raising the temperature to room temperature and further stirring for 30 minutes, an aqueous saturated ammonium chloride solution was added and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.0 g of the target compound.

Provenance & Evidence