Sodium Methoxide → Sodium Iodide

HRID 1801417ノート

反応式

HRID 1801417 の反応式
[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]

参加物

5

反応物 2

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-711200ebfcc64004ba60ff4814ccf88e
出典データセット
uspto-grants-2013_01
特許番号
US08349222B2

反応ノート

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