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 1801413노트

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HRID 1801413 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-779fb53da3304e478c2be6a36806467d
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349222B2

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