Sodium Hydroxide → HCID 67094441, compound

Participants

Reaction Conditions

Reaction Steps

3-Chloro-6-benzyloxy-5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester (1.33 g), methanol (27 ml) and 5M sodium hydroxide (27 ml) were refluxed for 2.5 hours. Methanol was evaporated and the resultant solid was filtered. The solid was dissolved in water and acidified with concentrated hydrochloric acid. The mixture was stirred in an ice-water bath, filtered and dried in vacuum. The resultant solid, copper (0.17 g) and quinoline (10.6 ml) were heated at 21° C. for one hour. To the cooled mixture was added 10% hydrochloric acid (26 ml) and dissolved in ethyl acetate. The solution was washed with 10% sodium carbonate and 1M hydrochloric acid and then it was evaporated to dryness. The residue, acetic acid (24 ml) and concentrate hydrochloric acid (3.2 ml) were refluxed 5 hours. The solution was evaporated to dryness. The residue was dissolved in diethyl ether and then extracted with 1M sodium hydroxide. The water phase was acidified with 6M hydrochloric acid and extracted into ethyl acetate. The solution was dried, evaporated to dryness and then triturated with diethyl ether and filtered.

Provenance & Evidence