2-Phenyl-1,3-dithiane → HCID 19843053, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-phenyl-1,3-dithiane (6.4 g, 32.7 mmol) in tetrahydrofuran (100 mL) at -40° C. under argon atmosphere was added 2.5M n-butyllithium (13.1 mL, 37.7 mmol). After 30 minutes the temperature was adjusted to -20° C. and maintained for 1.5 hour. The temperature of the dark brown solution was lowered to -78° C. and but-4-yne (1.5 g, 14.9 mmol) was added neat. After 1 hour, the temperature was raised to -60° C. for 1.5 hour and the solution was then stored at -20° C. overnight. The reaction mixture was poured onto water, the layers separated, and the aqueous layer was back-extracted with methylene chloride (2×50 mL). The combined organic extracts were washed with brine, dried (MgSO4) and the solvents evaporated at reduced pressure to give the product as an oil.

Provenance & Evidence