Acetone → HCID 21700362, compound

Temperature

25 °C

4.0 g (100 mmol) sodium hydride (60%) was added to a stirred solution of 13.8 g (50 mmol) 3-iodobenzoic acid ethyl ester and 12 mL (160 mmol) acetone in 25 mL anhydrous THF. The mixture was stirred at 25° C. for 20 min, then slowly warmed to 30° C. An exothermic reaction started, and the temperature was kept below 30° C. with water bath. After 1 h the hydrogen evolution stopped, and the mixture was cooled to 5° C., and quenched with 150 mL 3% aqueous hydrochloric acid. 200 mL ether was added to the solution, then the phases were separated. The organic phase was washed with 100 mL water three times, dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was mixed with 200 mL hexane, then the precipitate was filtered, and washed with 50 mL hexane three times. The filtrate was concentrated under reduced pressure, and purified by silica gel flash chromatography with hexane(neat), then hexane-EtOAc(4:1) as eluents to yield 7.0 g of the title compound, which was crystallized from hexane at −40° C.; TLC (Hexane-EtOAc(4:1)): Rf=0.65).

1. temperatureslowly warmed to 30° C
2. customAn exothermic reaction
3. customthe temperature was kept below 30° C. with water bath
4. temperaturethe mixture was cooled to 5° C.
5. customquenched with 150 mL 3% aqueous hydrochloric acid
6. addition200 mL ether was added to the solution
7. customthe phases were separated
8. washThe organic phase was washed with 100 mL water three times
9. dry with materialdried with anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationThe filtrate was concentrated under reduced pressure
12. additionThe residue was mixed with 200 mL hexane
13. filtrationthe precipitate was filtered
14. washwashed with 50 mL hexane three times
15. concentrationThe filtrate was concentrated under reduced pressure
16. custompurified by silica gel flash chromatography with hexane(neat)

ORD record

ord-669a08b2f892486e8ffcfa1f555212ce

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06294580B1