Acetic Acid → HCID 18351592, compound

Temperature

0 °C

Potassium t-butoxide (5.62 g) was dissolved in DMF (150 ml) and the obtained solution was cooled to 0° C. To this solution, methyl 2-(2-formyl-6-methoxyphenoxy)isovalerate (11.10 g) solution in DMF (50 ml) was added dropwise for 40 minutes, and the resulting solution was stirred for another 30 minutes. Acetic acid (4 ml) was added to the reaction solution and the solution was concentrated. The resultant was poured into water layer (300 ml) and extracted twice with ethyl acetate (150 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the obtained residue was dissolved in dichloromethane (250 ml). To this solution, Celite (70 g) and pyridinium dichromate (23.55 g) were added and the solution was stirred at room temperature for 19 hours. Isopropyl alcohol (20 ml) was added to the reaction solution and the solution was stirred for 15 minutes. Ether (200 ml) was added to the solution and the solution was filtered through Celite, followed by washing the obtained precipitate with ether (100 ml twice). The filtrate was concentrated and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=5/1-3/1) using silica gel to obtain the desired compound (7.26 g, yield: 66%).

1. concentrationthe solution was concentrated
2. additionThe resultant was poured into water layer (300 ml)
3. extractionextracted twice with ethyl acetate (150 ml)
4. washwashed with saturated brine
5. dry with materialby drying over sodium sulfate
6. customAfter removing the sodium sulfate
7. filtrationby filtration
8. customthe solvent was removed under reduced pressure
9. dissolutionthe obtained residue was dissolved in dichloromethane (250 ml)
10. additionTo this solution, Celite (70 g) and pyridinium dichromate (23.55 g) were added
11. stirringthe solution was stirred at room temperature for 19 hours
12. additionIsopropyl alcohol (20 ml) was added to the reaction solution
13. stirringthe solution was stirred for 15 minutes
14. additionEther (200 ml) was added to the solution
15. filtrationthe solution was filtered through Celite
16. washby washing the obtained precipitate with ether (100 ml twice)
17. concentrationThe filtrate was concentrated
18. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=5/1-3/1)

ORD record

ord-0ad24094982c44a492e27efe044c7b77

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06323235B1