Perchloric Acid → Pyrylium perchlorate

Participants

Reaction Steps

Using sodium hydride (2.0 g), p-(5-decyl-2-pyridinyl)-phenol (m.p. 90.4°-91.8° C.) (9 g) and 2S-2-(2'-tetrahydropyranyloxy)-4-methyl-pentyl-p-toluenesulfonate (10 g) obtained in Example 1-(2), and in the same manner as in Example 1-(3), the objective compound, S-1-(4-(5-decyl-2-pyridinyl)-phenoxy)-4-methyl-pentane-2-ol ([α]D24 6.4 (C0.5CHCl3)) (8.5 g) was obtained. In addition, the above-mentioned p-(5-decyl-2-pyridinyl)-phenol is obtained according to the process disclosed in Japanese patent application No. Sho 60-293934/1985 wherein p-methoxyphenyl-β-chlorovinyl ketone and N-dodecenylpiperidine as known substances are reacted together, followed by reacting the reaction product with perchloric acid to obtain pyrylium perchlorate, reacting this compound with ammonium acetate to obtain 5-decyl-2-(p-methoxyphenyl)pyridine, and further reacting this compound with aqueous hydrogen bromide in acetic acid for demethylation.

Provenance & Evidence