Cornforth reagent → HCID 68936960, compound

Participants

Reaction Conditions

Reaction Steps

The compound of Example 1C (1.1 g, 3.7 mmol) was dissolved in 5 mL of dichloromethane and cooled to 0° C.; 4.1 g of pyridinium dichromate was added, followed by 30 mg of pyridinium p-toluenesulfonate. The resultant mixture was stirred for 8 hours at 0° C.; an additional 1.8 g of pyridinium dichromate and 20 mg of pyridinium p-toluenesulfonate were added, and the mixture was allowed to warm to ambient temperature overnight. The mixture was diluted with ether and filtered through a pad of diatomaceous earth with an ether wash. The filtrate was washed with 1 N aqueous HCl, and then filtered through a plug of silica gel. The crude product was purified by chromatography on an Analogix Intelliflash 280™, eluting with a gradient of 10% to 15% ethyl acetate in hexanes to furnish the titled compound (1.0 g, 94%).

Provenance & Evidence