p-Toluenesulfonic acid → HCID 14969215, compound

Participants

Reaction Steps

To a solution of N-[2,6-bis(1-methylethyl)phenyl)-3-oxo-14-[(tetrahydro-2H-pyran-2-yl)oxyltetradecanamide (0.97 g, 0.001 mol; see Example 6 for preparation) in 190 mL 95% MEOH, p-toluenesulfonic acid (0.055 g, 0.15 eq) was added and the reaction mixture was stirred for 16 hours at room temperature under a nitrogen atmosphere. The reaction mixture was then concentrated in vacuo (30° C.) to give a tacky residue. This residue was diluted with water and chloroform, the layers were separated and the aqueous layer was then extracted three times with chloroform. The combined organic layers were then washed two times with saturated NaCl solution, dried (MgSO4), and concentrated in vacuo to yield 0.63 g (0.001 mol, 79.4%) of the desired product.

Provenance & Evidence