Hydrochloric Acid → HCID 22668864, compound

HRID 256809Notes

Reaction equation

[Li]CCCC.[O:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[F:11][CH:12]([F:33])[C:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:16]([CH:27]=[O:28])=[C:15]([C:29]([F:32])([F:31])[F:30])[N:14]=1.Cl>CCCCCC.CCOCC.O>[F:33][CH:12]([F:11])[C:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:16]([CH:27]([C:7]2[O:6][CH:10]=[CH:9][CH:8]=2)[OH:28])=[C:15]([C:29]([F:32])([F:30])[F:31])[N:14]=1

Participants

Conditions

Temperature: -6 °C

Procedure

To 2.5N n-BuLi in hexane (30 mL) cooled to 0 ° C was added in a slow stream furan (7 g, 0.1 mol) in anhydrous ether (60 mL). The mixture was heated at reflux for 3 h under a nitrogen atmosphere and then cooled to -6° C. A solution of methyl 2-(difluoromethyl)-5-formyl-4-(2-methylpropyl)-6-(trifluoromethyl)-3-pyridinecarboxylate (6 g, 17.6 mmol) in anhydrous ether (20 mL) was added dropwise and stirring was continued for 2 h. The mixture was then poured into iced water, acidified with conc. HCl and extracted with methylene chloride. The extract was washed with water and brine, dried (MgSO4), and conc. The oily residue was purified by chromatography with 10% ethyl acetate/cyclohexane to yield 4.4 g of methyl 2-(difluoromethyl)-5-(2-furanylhydroxymethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3-pyridinecarboxylate as an orange oil, a 61% yield. nD25 1.4863.

Workup

temperatureThe mixture was heated
temperatureat reflux for 3 h under a nitrogen atmosphere
extractionextracted with methylene chloride
washThe extract was washed with water and brine
dry with materialdried (MgSO4)
customconc. The oily residue was purified by chromatography with 10% ethyl acetate/cyclohexane

Sources & evidence

ORD record: ord-f9b4a091784f47e08799e62c04fe7610
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05260262

Reaction notes

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