Reaction #1256706

Reaction equation

3

4-(4-methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridin-1-ol

sodium hypophosphite hydrate

→

title compound

Yield 97.9%

4-(4-methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridine

Yield 97.9%

Solvents

acetic acid

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   Concentrationconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe resulting light-yellow oil was dissolved in chloroform (250 mL)
4. 4
   Washwashed successively with saturated NaHCO3 (aq.), water, and brine
5. 5
   OtherThe organic layer was then separated
6. 6
   Dryingdried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   OtherThe resulting pale-yellow solid was purified by flash chromatography on silica gel eluting with 1:1 hexane

Procedure

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.

Source