Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 54408141, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-phenyl-1-butenyl)-N-methyl-N-(tetrahydropyran-2-yloxy)benzamide (prepared in Example 1 Part E) (500 mg, 1.37 mmol) in 12 ml of CH3OH under argon was added pyridinium 4-toluenesulfonate (344 mg, 1.0 eq.). The mixture was heated to 55° C. and stirred for 2.5 hours. The solution was diluted with ether and washed with 1/2 saturate sodium chloride (20 ml) and brine (10 ml). The organic layer was dried over anhydrous MgSO4 and reduced to yield a light yellow oil which was flash chromatographed on Merck silica gel, eluting with (7:3) Hex:EtOAc. Product containing fractions were concentrated in vacuo to yield title product, 426 mg (85%) as a golden oil.

Provenance & Evidence