Acetic Acid → 5-Acetylfuro(2,3-c)pyridine

Temperature

60 °C

As 405 mg (7.5 mmol) of sodium methoxide was stirred in 5 mL of toluene, 1.16 g (10.0 mmol) of tert-butyl acetate was added dropewise at room temperature to the solution. Then, 956 mg (5.0 mmol) of 5-ethoxycarbonylfuro[2,3-c]pyridine dissolved in 5 mL of toluene was added dropwise at room temperature to the above solution. After all the solution had been added, the reaction mixture was heated to 60° C., a reaction was carried out for 3 hours. The resulting reaction mixture was then neutralized with 450 mg (7.5 mmol) of acetic acid, the solution was stirred for 30 minutes, 1.5 mL (7.5 mmol) of 5 N hydrochloric acid was then added, and the solution was stirred for 5 hours at 60° C. to carry out a reaction. The solution was then returned to room temperature, the organic layer was separated, the aqueous layer was extracted twice with 5 mL of methylene chloride, and the combined organic layer was dried with anhydrous magnesium sulfate and then concentrated in a rotary evaporator. The resulting solids were recrystallized from a mixed solvent of toluene-hexane, giving 580 mg (72% yield) of 5-acetylfuro[2,3-c]pyridine in a purity of 99% by HPLC.

1. additionwas added dropwise at room temperature to the above solution
2. additionAfter all the solution had been added
3. customThe resulting reaction mixture
4. stirringthe solution was stirred for 5 hours at 60° C.
5. customa reaction
6. customwas then returned to room temperature
7. customthe organic layer was separated
8. extractionthe aqueous layer was extracted twice with 5 mL of methylene chloride
9. dry with materialthe combined organic layer was dried with anhydrous magnesium sulfate
10. concentrationconcentrated in a rotary evaporator
11. customThe resulting solids were recrystallized from a mixed solvent of toluene-hexane

ORD record

ord-89b75ad41dfd427e9cc851cfdb970c06

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265580B1