Pyridinium → HCID 85303357, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the alkyne 12b (526 mg, 457 μmol) in absolute ethanol (6.0 mL) was added pyridinium p-toluenesulfanate (273 mg, 1.09 mmol) in one portion. The reaction mixture was stirred at 55° C. overnight (~14 h). The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (50 mL). The organic solution was washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was purified by MPLC (3:1 hexane:ethyl acetate) to give the alcohol 14 (387 mg, 92%); IR (neat, thin layer): 3405, 3070, 3048, 2935, 2858, 1963, 1893, 1827, 1589, 1507, 1471, 1428, 1365, 1228, 1155, 1002, and 823 cm-1 ; Anal. Calcd for C58 H74O6Si2 : C, 75.44%; H, 8.08%. Found: C, 75.16%; H, 7.89%; tlc: Rf =0.14 in 3:1 hexane:ethyl acetate; [α]DRT =-7.9°, c=5.47 in ethyl acetate.

Provenance & Evidence