Hydrochloric Acid → HCID 15113951, compound

Participants

Reaction Steps

n-Butyl lithium (a 2.5M solution in hexane; 4.37 ml, 10.9 mmol) was added to a solution of morpholine (0.91 ml, 10.4 mmol) in tetrahydrofuran (30 ml) at -78° under argon. After 20 min., 3-furaldehyde (0.91 ml, 10.4 mmol) was added. After another 20 min., sec-butyl lithium (a 1.3M solution in cyclohexane; 8.4 ml, 10.9 mmol) was added dropwise and stirring continued at -78° for 4 hours before a solution of 4-bromobenzaldehyde (2.11 g, 11.4 mmol) in tetrahydrofuran (10 ml) was added. Stirring was continued overnight (17 hours) while the cooling bath was allowed to attain room temperature. The solution was poured into ice cold 10% (v/v) hydrochloric acid (30 ml) and after stirring at 0° for 10 min., the layers were separated. The aqueous phase was extracted with diethyl ether. All the organic phases were combined, dried (magnesium sulfate) and evaporated down to give an oil, which was purified by flash chromatography on silica using 40% ethyl acetate/hexane. Fractions with Rf of about 0.23 on evaporation gave the title compound as a yellow solid, m.p. 83°-4° (recrystallized from chloroform).

Provenance & Evidence