Hydrochloric Acid → HCID 18469814, compound

Participants

Reaction Steps

A solution of 4-Hydroxymethyl-4-methoxymethyl-1,2-dithiacyclopentane (0.1 g) in THF (20 ml) was added to a suspension of sodium hydride (0.03 g) in THF (20 ml) and the mixture was stirred at room temperature for 30 min. Ethylene sulfate (0.14 g) was added and the resulting mixture stirred at room temperature for 48 h. Hydrochloric acid (3M, 5 ml) was added, and the aqueous layer extracted with ethyl acetate (5×20 ml). The organic layers were combined and washed with water (50 ml) and dried (Na2SO4). The solvent was removed under reduced pressure and the resulting oil purified by flash chromatography (ethyl acetate-light petroleum, 1:1 as eluant) to give 4-(2-hydroxyethoxy)methyl-4-methoxymethyl-1,2-dithiacyclopentane (66.8 mg, 54%). 1H-n.m.r. (CDCl3) δ2.93 (AB quartet, 4H), 3.34 (s, 3H), 3.36 (s, 2H), 3.46 (s, 2H), 3.56 (m, 2H). 3.70 (m, 2H); 13C-n.m.r. (CDCl3) δ44.7, 56.2, 59.3, 61.6, 72.2, 72.3, 74.2; m/z 224 (M+)

Provenance & Evidence