2,6-Di-tert-butyl-4-methylpyridine → HCID 20615194, compound
Reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.[F:32][C:33]([F:45])([F:44])[C:34](OS(C(F)(F)F)(=O)=O)=[O:35]>C(Cl)(Cl)(Cl)Cl>[CH2:1]([CH:4]1[CH2:5][CH2:6][CH:7]([CH:10]2[CH2:15][CH2:14][C:13]([O:16][C:34](=[O:35])[C:33]([F:45])([F:44])[F:32])=[CH:12][CH2:11]2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]Participants
Procedure
To 50 ml of carbon tetrachloride were added 3.9 g (18 mmol) of 4-(4-propylcyclohexyl)cyclohexanone and 3.8 g (19 mmol) of 2,6-di-t-butyl-4-methylpyridine, and the mixture was stirred at room temperature. To this mixture was added dropwise 2 ml of solution of 4.5 g (18 mmol) of trifluoroacetyltriflate in carbon tetrachloride. Subsequently, 25 ml of carbon tetrachloride was added thereto and the mixture was stirred at room temperature for 1 hour. The reaction solution was filtered off and then the filtrate was concentrated under a reduced pressure. After the residue was purified by column chromatography on silica gel (eluent: heptane/toluene=3/1), the solvent was distilled off, and the residue was subjected twice to recrystallization by using heptane to give 1.3 g (4.1 mmol) of trifluoroacetic acid 4-(4-propylcyclohexyl)-1-cyclohexenyl ester. Yield of this compound based on 4-(4-propylcyclohexyl)cyclohexanone was 23%.
Workup
- stirringthe mixture was stirred at room temperature for 1 hour
- filtrationThe reaction solution was filtered off
- concentrationthe filtrate was concentrated under a reduced pressure
- customAfter the residue was purified by column chromatography on silica gel (eluent: heptane/toluene=3/1)
- distillationthe solvent was distilled off
- customthe residue was subjected twice to recrystallization
Sources & evidence
- ORD record
- ord-f884044bedc945e9860c99afd4b70ae8
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06685995B1
Reaction notes
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