Sodium Methoxide → Sodium Iodide

HRID 1801417Notes

Reaction equation

HRID 1801417 reaction equation
[I-:1].[OH:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[C:15]([CH3:16])=[CH:14][N+:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])=[C:5]([CH3:19])[CH:4]=1.C[O-].[Na+:22]>CO>[CH3:9][C:7]1[C:6](=[C:10]2[C:11]([CH3:18])=[CH:12][N:13]([CH3:17])[CH:14]=[C:15]2[CH3:16])[C:5]([CH3:19])=[CH:4][C:3](=[O:2])[CH:8]=1.[Na+:22].[I-:1]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 669936364-(4-Hydroxy-2,6-dimethyl-phenyl)-1,3,5-trimethyl-pyridinium iodide

Product 2

HCID 5238Sodium IodideYield 98%HCID 669933403,5-dimethyl-4-(1,3,5-trimethyl-1H-pyridin-4-ylidene)-cyclohexa-2,5-dienone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe resulting solid was then recrystallized from anhydrous methanol/THF

Sources & evidence

ORD record
ord-711200ebfcc64004ba60ff4814ccf88e
Source dataset
uspto-grants-2013_01
Patent number
US08349222B2

Reaction notes

Loading…