Methyl formate → HCID 19852111, compound

HRID 1607232Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]([F:39])([F:38])[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([N:25]2[CH2:29][CH:28]([CH3:30])[C:27]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)=[N:26]2)=[O:24])=[CH:18][CH:17]=1.[CH:40](OC)=[O:41]>O1CCCC1.CCCCCC.C(O)(=O)C>[F:39][C:14]([F:13])([F:38])[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([N:25]2[CH2:29][C:28]([CH:40]=[O:41])([CH3:30])[C:27]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)=[N:26]2)=[O:24])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: -20 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-882bb59e6ef34b348be5635b4728e2ea
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863947

Reaction notes

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