4-(4-Methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridin-1-ol → 4-(4-Methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridine

HRID 1801413ノート

反応式

HRID 1801413 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[C:15]([CH3:16])=[CH:14][N:13](O)[CH2:12][C:11]=2[CH3:18])=[C:5]([CH3:19])[CH:4]=1.O.[PH2]([O-])=O.[Na+]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:19])[C:6]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[CH:12][C:11]=2[CH3:18])=[C:7]([CH3:9])[CH:8]=1

参加物

5

反応物 2

HCID 669931454-(4-Methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridin-1-olHCID 178418950HCID 178418950、化合物

生成物 1

HCID 595503344-(4-Methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridine収率 97.9%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 3 (6.55 g, 25.5 mmol) and palladium (10 wt. % on activated carbon; 3.05 g, 2.8 mmol) in acetic acid (150 mL) was added sodium hypophosphite hydrate (6.7 g, 63 mmol) in a single portion at 80° C. The reaction mixture was stirred at 80° C. under N2 for 12 h, then filtered and concentrated in vacuo. The resulting light-yellow oil was dissolved in chloroform (250 mL) and washed successively with saturated NaHCO3 (aq.), water, and brine. The organic layer was then separated, dried over MgSO4, filtered, and concentrated in vacuo. The resulting pale-yellow solid was purified by flash chromatography on silica gel eluting with 1:1 hexane:ethyl acetate, to give 6.01 g (97.9%) of the title compound as colorless solid: mp 87-88° C.; 1H NMR (400 MHz, CD2Cl2): δ 8.334 (s, 2H), 6.707 (s, 2H), 3.804 (s, 3H), 1.892 (s, 6H), 1.851 (s, 6H); 13C NMR (100 MHz, CD2Cl2): δ 159.330, 148.939, 148.420, 136.373, 131.905, 129.958, 113.489, 55.556, 20.188, 16.831; MS (APCI): m/z 242.2 [(M+H)+,100]; Anal. Calcd. For C16H19NO: C, 79.63; H, 7.94; N, 5.80. Found: C, 79.39; H, 7.94; N, 5.75.

後処理

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting light-yellow oil was dissolved in chloroform (250 mL)
  4. washwashed successively with saturated NaHCO3 (aq.), water, and brine
  5. customThe organic layer was then separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting pale-yellow solid was purified by flash chromatography on silica gel eluting with 1:1 hexane

出典と根拠

ORDレコード
ord-779fb53da3304e478c2be6a36806467d
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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