Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | 4-(4-Hydroxy-2,6-dimethyl-phenyl)-1,3,5-trimethyl-pyridinium iodide | HCID 66993636 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Sodium Iodide | HCID 5238 | 98% |
| Product | 3,5-dimethyl-4-(1,3,5-trimethyl-1H-pyridin-4-ylidene)-cyclohexa-2,5-dienone | HCID 66993340 | — |
Reaction Steps
To the methylpyridinium iodide salt 7 (0.184 g, 0.500 mmol) was added dropwise a solution of sodium methoxide in methanol (1.2 mL, 0.5 M). The color of the mixture immediately changed from yellow to red. After stirring at room temperature for 10 min, the solvent was removed under reduced pressure. The resulting solid was then recrystallized from anhydrous methanol/THF to afford the orange title compound as a complex with NaI (0.382 g, 98%): 1H NMR (400 MHz, DMSO-d6): δ 8.818 (s, 2H), 5.983 (s, 2H), 4.265 (s, 3H), 2.055 (s, 6H), 1.566 (s, 6H); 13C NMR (100 MHz, DMSO-d6): δ 161.235, 142.173, 137.851, 132.019, 118.598, 114.039, 46.917, 19.574, 16.754; MS (ESI): m/z 242.4 [(M+H)+,100]; HRMS (EI): m/z 241.1463 [M+]; calcd, 241.1467. Anal. Calcd. for C16H19NO.NaI: C, 49.12; H, 4.90; N, 3.58. Found; C, 49.04; H, 5.40; N, 3.49.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08349222B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-711200ebfcc64004ba60ff4814ccf88e |
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| Source note | uspto-grants-2013_01 |
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