Ethylene Glycol → HCID 21849014, compound

Participants

Reaction Steps

15 g (0.048 mol) of the title compound of Step C, 150 mL of ethylene glycol, 100 mL of trimethyl orthoformate (purchased from Aldrich Chemical Company), and 0.06 g of p-toluenesulfonic acid monohydrate were stirred together at 80° C. under nitrogen overnight. The mixture was diluted with 250 mL of diethyl ether and washed with a 1:1 mixture of 1N sodium hydroxide:saturated aqueous NaCl (2×300 mL), saturated aqueous NaCl (1×500 mL), dried (Na2SO4), filtered, and evaporated to dryness. The crude product was chromatographed over silica gel eluting with a mixture of ethyl acetate:hexane (0.5:9.5) to yield 8.39 g of the title compound of Step D as a solid melting at 152-153° C. 1H NMR (CDCl3): δ2.3 (m,2H), 3.0 (m,2H), 4.16 (m,2H), 4.37 (m,2H), 7.6 (s,1H).

Provenance & Evidence