Ammonium Chloride → HCID 59355151, compound

Participants

Reaction Conditions

Reaction Steps

A −78° C. solution of 9 (10 mg, 0.02 mmol) in THF (0.4 mL) was treated with tert-BuLi (60 μL, 0.01 mmol, 1.7 M/pentane). After 30 min., 2 mL saturated NH4Cl solution was added and the resulting mixture was extracted with dichloromethane (3×20 mL). The combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. The crude product still contained vinyl bromide 9 and so was resubmitted to the reaction conditions: THF (0.2 mL) and tert-BuLi (100 mL,) were added and the reaction was stirred for 3 h at −40° C. and then worked up as above. Purification by flash chromatography on silica gel (0%→30% MeOH/CH2Cl2) gave compound 11 (4 mg, 0.01 mmol, 50%).

Provenance & Evidence