Water → HCID 21543761, compound

Participants

Reaction Steps

Sodium (0.595 g., 0.026 mole) is dissolved in absolute ethanol (20 ml.). N-(β ,β-dichloroethyl) (3-trifluoromethylphenoxy) (4-chlorophenyl)acetamide (4.69 g., 0.011 mole) is then added and the solution refluxed for 20 minutes. A precipitate forms and the solution becomes dark orange and then brown. The reaction mixture is cooled in an ice bath and then diluted with 50 ml. of water. The solution is extracted with 50 ml. of ether and then with 2 × 25 ml. of ether. The ether extracts are combined and washed successively with a sodium hydroxide solution (2 × 25 ml., 1 N), hydrochloric acid (2 × 25 ml., 1 N) and then with water until neutral. The ether solution is then washed with a saturated sodium chloride solution (25 ml.), treated with charcoal and then filtered to remove the charcoal. The ether solution is then dried over anhydrous magnesium sulfate, filtered and the ether removed under vacuum to afford 3.24 g. of an orange oil. The orange oil is dissolved in chloroform and chromatographed on a silica gel column employing as the eluant a mixture of chloroform and ethyl acetate (20:1). One ml. portions are collected and analyzed by thin layer chromatography and IR. The first 32 ml. collected contain no product. The next 18 ml. contain a mixture of starting material and final product. The next 53 ml. contain 2.03 g. of product obtained by evaporation of the solvent. Recrystallization from n-hexane affords 2-[α-(3-trifluoromethylphenoxy) 4-chlorobenzyl]oxazole, m.p. 66°-67°C.

Provenance & Evidence