Reaktion #599277

Reaktionsgleichung

20

4-(benzyloxy)-3-heptyl-5-methoxy-2,6-dimethylpyridine

mCPBA

→

3-heptyl-1-hydroxy-5-methoxy-2,6-dimethylpyridin-4(1H)-one

Lösungsmittel

EtOH

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe solution was washed with aqueous NaHCO3
2. 2
   Trocknendried over anhydrous MgSO4
3. 3
   Einengenconcentrated under diminished pressure
4. 4
   Sonstigeto afford a crude residue
5. 5
   FiltrationAfter filtration through celite, which
6. 6
   Waschenwas thoroughly washed with EtOH
7. 7
   Einengenthe filtrate was concentrated under diminished pressure
8. 8
   Sonstigepurified by chromatography on a silica gel column
9. 9
   WaschenElution with 20:1 ethyl acetate/methanol

Vorschrift

A solution of 20 (19 mg, 0.66 mmol) and mCPBA (125 mg, 0.72 mmol) in anhydrous CH2Cl2 (2 mL) was stirred at 0° C. for 1 hr under argon atmosphere, the solution was washed with aqueous NaHCO3 dried over anhydrous MgSO4 and concentrated under diminished pressure to afford a crude residue. The residue was dissolved in EtOH, Pd/C was added and after applying an H2 atmosphere (1 bar), the solution was stirred at room temp for 30 min, After filtration through celite, which was thoroughly washed with EtOH, the filtrate was concentrated under diminished pressure and purified by chromatography on a silica gel column. Elution with 20:1 ethyl acetate/methanol gave 3-heptyl-1-hydroxy-5-methoxy-2,6-dimethylpyridin-4(1H)-one (CPD-5) as a light yellow oil; yield 9 mg (61%); silica gel TLC Rf 0.25 (3:1 ethyl acetate/methanol); 1H NMR (CDCl3) δ 0.84-0.89 (m, 3H), 1.24-1.35 (m, 10H), 2.45 (s, 3H), 2.50 (s, 3H) 2.63-2.67 (m, 2H) and 3.74 (s, 3H).

Quelle