Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 57026977, compound

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Reaction Conditions

Reaction Steps

The crude compound of Example 3E (0.96 g) was dissolved in 19 mL of dichloromethane and cooled to 0° C.; 3.1 g of pyridinium dichromate was added, followed by 22 mg of pyridinium p-toluenesulfonate. The resultant mixture was stirred for 1.5 hours at 0° C.; an additional 1.3 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 8% to 15% ethyl acetate in hexanes. Fractions containing the titled compound were combined and concentrated in vacuo (0.77 g, 96%, 2 steps).

Provenance & Evidence