Hydrochloric Acid → HCID 14154277, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3.01 g (7.58 mmol) of 2-(4,5-dibromo-3-isopropylthio-2-furanyl)-4,4-dimethyloxazoline and aqueous 4N HCl is warmed at reflux under N2 atmosphere for 0.5 hr. The reaction is cooled to 0° C. and treated with methanol (60 mL), tetrahydrofuran (30 mL), and 4.25 g (177.0 mmol) of anhydrous LiOH. The reaction is stirred at 0° C. for 2 hr and 25° C. for 16 hr, then concentrated in vacuo. The resulting residue is dissolved in H2O and extracted with diethyl ether (2X). The aqueous solution is acidified with aqueous 10% HCl and extracted with ethyl acetate (4X). The combined extracts are washed with aqueous saturated NaCl, dried (Na2SO4), and concentrated in vacuo to afford 1.63 g (2.61 g theo.; 62%) of the carboxylic acid as a beige solid. Recrystallization from diethyl ether/hexane affords an analytical sample; mp 130°-131° C.

Provenance & Evidence