Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 57814828, compound

Participants

Reaction Conditions

Reaction Steps

A 20 mL vial equipped with a magnetic stirbar was charged with 175 mg (0.34 mmol) of TAP-ether 8 dissolved in 5 mL of methanol. To this was then added 300 mg (1.20 mmol) of pyridinium p-toluenesulfonate and the mixture was stirred at 22° C. over 7.5 h. The reaction was sampled by TLC (Rf of product was 0.6 in EtOAc) and worked up by concentration in vacuo to remove methanol. The residual products were taken up in ethyl acetate and filtered through a 22 g plug of silica gel, eluting the polar product away from the salts with ethyl acetate (350 mL). Concentration of the filtrate yielded 125 mg of product triol 9 as an oil; 1H NMR (CDCl3): 1.18 (d, J=6.3 hz, 3H), 1.34-1.62 (m, 5H), 1.69 (m, 2H), 1.84-2.38 (m, 11H), 2.47 (br s, 1H), 3.53 (br s, 1H), 3.70 (br s, 1H), 3.79 (br m, 1H), 3.99 (m, 1H), 4.08 (m, 2H), 4.57 (m, 2H), 5.18-5.60 (m, 6H), 5.91 (m, 1H).

Provenance & Evidence