p-Toluenesulfonic acid → HCID 19434047, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the product from Step C (106.9 g, 0.521 mol) in THF (360 mL) was cooled to 0° C. and para-toluenesulfonic acid (3.6 g) was added. Ethyl vinyl ether (250 mL, 2.6 mol) was added over a period of 1.75 hr while maintaining the temperature of the reaction mixture below 5° C. The yellow solution was stirred at 0° C. for 1 hr, a saturated aqueous sodium bicarbonate solution (400 mL) was added and this mixture was extracted with ethyl acetate (3×250 ml). The combined extracts were dried (Na2SO4) and evaporated to give a residue which was purified by column chromatography (silica, hexane to 20% hexane/ethyl acetate) to give the desired product (78%) as a light yellow oil. This material was used in the next step.

Provenance & Evidence