Hydrochloric Acid → HCID 15113951, compound

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).

1. waitAfter another 20 min.
2. addition8.4 ml, 10.9 mmol) was added dropwise
3. additionwas added
4. stirringStirring
5. waitwas continued overnight
6. custom(17 hours)
7. customto attain room temperature
8. stirringafter stirring at 0° for 10 min.
9. customthe layers were separated
10. extractionThe aqueous phase was extracted with diethyl ether
11. dry with materialdried (magnesium sulfate)
12. customevaporated down
13. customto give an oil, which
14. customwas purified by flash chromatography on silica using 40% ethyl acetate/hexane
15. customFractions with Rf of about 0.23 on evaporation
16. customgave
17. customthe title compound as a yellow solid, m.p. 83°-4° (recrystallized from chloroform)

ORD record

ord-aab5354944a646b8b21c3ed3a22d09cb

Source dataset

uspto-grants-1990_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04935530