Réaction #992715

Équation de réaction

NaH

3-hydroxylpyridine

2-bromoacetophenone

→

1-Phenyl-2-(pyridine-3-yloxy)-ethanone

Rendement 75.0%

Solvants

DMF

DMF

DMF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe resulting mixture was stirred for 5 h until the starting material
2. 2
   Autreconsumed
3. 3
   workup.ADDITIONWater was added
4. 4
   Autreto quench
5. 5
   Autrethe reaction
6. 6
   Extractionthe aqueous phase was extracted with CH2Cl2 (3×40 mL)
7. 7
   LavageThe combined organic phases were washed with brine
8. 8
   Séchagedried over MgSO4
9. 9
   Concentrationconcentrated under reduced pressure
10. 10
    AutreThe residue was purified by flash column chromatography
11. 11
    Lavageeluted by hexane:ethyl acetate (1:1)
12. 12
    Autrethe correct product was obtained as a white solid

Mode opératoire

To a suspension NaH (0.8 g, 60%, 20 mmol) in DMF (15 mL) was added a solution of 3-hydroxylpyridine (1.9 g, 20 mmol) in DMF (10 mL) at ° C. under nitrogen. After the mixture was stirred 15 min, a solution of 2-bromoacetophenone (3.98 g, 20 mmol) in DMF (10 mL) was added dropwise. The resulting mixture was stirred for 5 h until the starting material consumed. Water was added to quench the reaction and the aqueous phase was extracted with CH2Cl2 (3×40 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography eluted by hexane:ethyl acetate (1:1) and the correct product was obtained as a white solid; mp 81-82° C.; yield 75% (3.19 g); H NMR (400 MHz, CDCl3): d 5.40 (s, 2H, OCH2), 7.28 (m, 2H, Ar), 7.59 (m, 2H, Ar), 7.67 (m, 1H, Ar), 8.03 (m, 2H, Ar), 8.32 (m, 1H, Ar), 8.43 (m, 1H, Ar); CNMR (100 MHz, CDCl3): δ 70.8, 121.7, 123.9, 128.1, 129.0, 134.2, 134.3, 138.2, 143.1, 154.4, 193.6; IR ν (cm−1) 3054, 3007, 2988, 2963, 2898, 1702, 1579, 1486, 1450, 1422, 1275, 1263, 1233, 1090, 974, 815, 765, 751.

Source