Methyl formate → HCID 19852111, compound

Temperature

-20 °C

To 3.5 ml of diisopropylamine dissolved in 20 ml of tetrahydrofuran and cooled in a -20° C. bath was added 10.0 ml of a 2.5 molar solution n-butyllithium in hexane. After stirring for 5 minutes a solution of 4.0 g of N-(4-trifluoromethoxyphenyl)-3-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide in 10 ml of tetrahydrofuran was added and the resulting solution stirred for 15 minutes and then cooled to -78° C. To this solution was added 2.0 ml of methyl formate and, after 5 minutes, 2 ml of acetic acid was added. The reaction mixture was partitioned between diethyl ether and water and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 3.9 g of N-(4-trifluoromethoxyphenyl)-3-(4-chlorophenyl)-4-formyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide. NMR and IR data were consistent with the structure.

1. additionwas added
2. temperaturecooled to -78° C
3. waitafter 5 minutes
4. customThe reaction mixture was partitioned between diethyl ether and water
5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
6. filtrationThe resulting solution was filtered
7. customevaporated in vacuo

ORD record

ord-882bb59e6ef34b348be5635b4728e2ea

Source dataset

uspto-grants-1989_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04863947