Sodium hydride → HCID 20271453, compound

Participants

Reaction Steps

A solution of 3-hydroxy-2-(3-cyanopropyl)-5-methylpyridine from Example 3(a) (1.5 g), in dimethyl sulphoxide (11 ml) was first treated with sodium hydride (0.2 g) and then with n-propyl iodide in dimethyl sulphoxide (3 ml) at 17°-20° C. After stirring for four hours at room temperature, the solvent was removed in vacuo and the residue partitioned between chloroform and water, the chloroform extract was evaporated to dryness to give 3-n-propyloxy-2-(3-cyanopropyl)-5-methylpyridine (1.79 g) N.M.R. (CDCl3), assignment, δ(p.p.m.), multiplicity; O(CH2)2CH3, 1.07; t; OCH2CH2CH3, 1.86; m; CH2CH2CN, 2.12, m; CH2CN, 2.40, m; 5-CH3, 2.30, s; CH2 (CH2)2CN, 3.94, m; OCH2, 3.91, t; 4-H pyridyl, 6.96, m; 6-H pyridyl, 7.91, m;

Provenance & Evidence