Ethanol → HCID 15457086, compound
Reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([Cl:13])=[CH:11][C:10]([F:14])=[C:9]([C:15]3[C:16](=[O:26])[N:17]([CH3:25])[C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=3)[C:7]=2[CH:8]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH2:32](O)[CH3:33]>>[Cl:13][C:12]1[C:6]2[O:5][C:4]([C:1]([O:3][CH2:32][CH3:33])=[O:2])=[CH:8][C:7]=2[C:9]([C:15]2[C:16](=[O:26])[N:17]([CH3:25])[C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=2)=[C:10]([F:14])[CH:11]=1Participants
Procedure
0.08 g (0.21 mmol) of 3-(2-carboxy-7-chloro-5-fluorobenzofuran-4-yl)-1-methyl-6-trifluoromethyl-2-(1H)-pyridone was dissolved in 10 ml of ethanol, and 4.0 mg (0.04 mmol) of sulfuric acid was added thereto, followed by refluxing for 2 hours. Ethanol was distilled off under reduced pressure. Then, the obtained residue was poured into water and extracted with diethyl ether. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Diethyl ether was distilled off under reduced pressure. Then, the obtained crude crystals were washed with n-hexane to obtain 0.09 g (yield: 99%) of the desired product. Melting point: 118-120° C. 1H-NMR (300 MHz, CDCl3) δ value: 1.41(3H,t), 3.75(3H,s), 4.43(2H,q), 6.82(1H,d), 7.34(1H,d), 7.38(1H,s), 7.57(1H,d)ppm.
Workup
- temperatureby refluxing for 2 hours
- distillationEthanol was distilled off under reduced pressure
- additionThen, the obtained residue was poured into water
- extractionextracted with diethyl ether
- washAfter washing with water
- dry with materialthe organic layer was dried over anhydrous magnesium sulfate
- distillationDiethyl ether was distilled off under reduced pressure
- customThen, the obtained crude crystals
- washwere washed with n-hexane
Sources & evidence
- ORD record
- ord-4686442d63c6494bbc2e327cc9f2170e
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265349B1
Reaction notes
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