p-Nitroacetophenone → HCID 11031413, compound

18-Crown-6 (41.6 g) was added to a toluene (484 ml) solution of trimethyl phosphonoacetate (22.6 ml) in a nitrogen atmosphere. An 11% potassium hexamethyldisilazide (hereinafter referred to as “KHMDS”)/toluene solution (315 ml) was added thereto, and the obtained mixture was stirred for 1 hour. Under ice-cooling, 4-nitroacetophenone (20 g) was added thereto, and the mixture was stirred for 1 hour. After the reaction was over, the reaction was stopped with a saturated ammonium chloride solution. The reaction mixture was separated with ethyl acetate and water. The organic layer was washed three times with water and once with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was suspended in methanol (40 ml) and stirred. The precipitated solid was filtered off and washed with cold methanol. Thus, Compound 6a (12.4 g, 46%) was obtained as an opalescent solid.

1. additionwas added
2. temperatureUnder ice-cooling
3. stirringthe mixture was stirred for 1 hour
4. customThe reaction mixture was separated with ethyl acetate and water
5. washThe organic layer was washed three times with water
6. dry with materialonce with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate
7. distillationAfter the solvent was distilled off
8. stirringstirred
9. filtrationThe precipitated solid was filtered off
10. washwashed with cold methanol

ORD record

ord-4e1abc231d0e4d6fb1cb0ef1bce0716c

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855300B2