S-Methyl methanethiosulfonate → HCID 19602330, compound

Participants

Reaction Steps

To a solution of the product of Example 8 (1.1 g, 4 mmol) in 20 mL THF at <-60° C. under a positive nitrogen atmosphere was added dropwise 2.5M of n-BuLi in hexane (2.2 mL) at <-60° C., and the solution was stirred for 0.5 h. A solution of methyl methanethiolsulfonate (0.6 g, 4.8 mmol) in 2 mL THF was added at <-60° C. After 1 h at ambient temperature, the solution was poured into ice water and extracted with methylene chloride. The organic layer was washed with brine, dried, and concentrated in vacuo. The residue was purified on a silica gel column using 8% ethyl acetate-hexane to give 1 g of the desired product as a viscous yellow oil, a yield of 76.9%. nD24 1.5886.

Provenance & Evidence