Dimethyl Sulfide → HCID 19603849, compound

Participants

Reaction Steps

To a 0° C. solution of 2-methyl-2-butene (2M in THF, 14 mL, 28 mmol) in THF (20 mL) was added BH3.DMS (10 M in DMS, 1.4 mL, 14 mmol). After 30 min, the solution was allowed to warm to room temperature for 1 h, then cooled to -40° C. A stream of propyne (large excess) was passed through the solution, and the solution was allowed to warm to 0° C., then concentrated. 14b (100 mg, 0.31 mmol), Pd2 (dba)3)(14 mg, 0.014 mmol) and triphenylphosphine (18 mg, 0.068 mmol) were added, and the mixture was dissolved in 20 mL of 3:1:1 toluene:nPrOH:water. Et2NH (0.5 mL, 4.8 mmol) was added, the solution was degassed, and heated to reflux for 3 h. The mixture was cooled and partitioned between EtOAc and saturated aqueous NH4Cl. The organic phase was washed with brine, dried over MgSO4 and evaporated. Purification by flash chromatography (20% EtOAc/hexanes to 40% EtOAc/hexanes) provided 38 mg of the title compound.

Provenance & Evidence