(Dimethyl sulfide)trihydroboron → HCID 67692931, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 11 (39.9 g, 0.021 mol) in THF (400 ml) under N2 was added dropwise 10M borane dimethylsulfide (42.5 ml, 0.42 mol). After addition, the reaction which was fitted with a short-path distillation head was heated to 60° C. for 3 h while collecting distilled dimethylsulfide and THF. The solution was then concentrated to dryness and then 6N HCl was carefully added dropwise. After addition the reaction was heated at reflux for 1/2 h, the solution was concentrated, flushed with EtOH (2×) and the residue was then carefully treated with saturated NaHCO3. The aqueous layer was extracted with EtOAc (4×) and the organic extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on a Still column (120 mm) packed with silica gel and eluted with 20:1 CHCl3 --CH3OH to yield 15.4 g (40%) of trans -12 and then 4.7 g (12%) of cis-13.

Provenance & Evidence