Acetic Acid → HCID 11288425, compound

Temperature

0 °C

THF (10 ml) was added to zinc powder (5.92 g) and then a catalytic amount of iodine was added. While vigorously stirring the resulting solution, a small amount of a solution of 7-methoxy-3-oxo-2-(2-propenyl)-2,3-dihydrobenzofuran (6.16 g) and methyl bromoacetate (8.9 ml) in THF (90 ml) was added at room temperature. After confirming generation of heat, the reaction solution was cooled to 0° C. and the remainder of the solution was added dropwise for 15 minutes. The reaction solution was stirred at 0° C. for 3 hours, cooled to room temperature and was stirred for another 2.5 hours. Acetic acid (5.5 ml) was added to the reaction solution and the resultant was filtered through Celite. After removing the solvent under reduced pressure, the residue was dissolved in toluene (100 ml) and p-toluenesulfonic acid (536 mg) was added thereto, followed by stirring the resulting mixture at room temperature for 2 hours. The reaction solution was poured into water (150 ml) and the resultant was extracted twice with ethyl acetate (50 ml). After combining the organic layers, the resultant was washed with saturated aqueous sodium hydrogen carbonate solution and with saturated brine, and dried over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1) using a silica gel to obtain the desired compound (5.23 g, yield: 67%).

1. temperatureof heat
2. additionthe remainder of the solution was added dropwise for 15 minutes
3. stirringThe reaction solution was stirred at 0° C. for 3 hours
4. temperaturecooled to room temperature
5. stirringwas stirred for another 2.5 hours
6. filtrationthe resultant was filtered through Celite
7. customAfter removing the solvent under reduced pressure
8. dissolutionthe residue was dissolved in toluene (100 ml)
9. additionp-toluenesulfonic acid (536 mg) was added
10. stirringby stirring the resulting mixture at room temperature for 2 hours
11. additionThe reaction solution was poured into water (150 ml)
12. extractionthe resultant was extracted twice with ethyl acetate (50 ml)
13. washthe resultant was washed with saturated aqueous sodium hydrogen carbonate solution and with saturated brine
14. dry with materialdried over sodium sulfate
15. customAfter removing the sodium sulfate
16. filtrationby filtration
17. customthe solvent was removed under reduced pressure
18. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1)

ORD record

ord-ae4afde84d88475dba9399b63504f8c8

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06323235B1