Cornforth reagent → HCID 14281472, compound

Participants

Reaction Steps

Pyridinium dichromate (64.45 g, 171.33 mmol) was added to a solution of 6-[2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]ethyl]-6-ethyl-2-cyclohexenol (56.01 g, 137.06 mmol) in 274 mL of dry N,N-dimethylformamide at 0° C. under nitrogen. After 1 hour, the reaction was poured into 2L of brine and extracted with 10×500 mL of ether. The ethereal solutions were concentrated in vacuo and flash chromatographed in two batches (95 mm column, 51/2 inches of silica gel, 8% ethyl acetate in petroleum ether eluent) to afford 48.94 g (88%) of product as a pale yellow oil.

Provenance & Evidence