Reaktion #599276

Reaktionsgleichung

NH4Cl

iodo

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

sodium methoxide

sodium

→

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

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   ExtraktionThe mixture was extracted with portions of ethyl ether
3. 3
   TrocknenThe combined organic phase was dried over anhydrous MgSO4
4. 4
   Einengenconcentrated under diminished pressure
5. 5
   Sonstigeto afford a crude residue
6. 6
   WaschenElution with ethyl acetate

Vorschrift

To a solution of sodium methoxide prepared from sodium (5.0 mg, 0.23 mmol) and MeOH (1 mL) were added the iodo derivative 19 (27 mg, 0.06 mmol) and CuI (1.66 mg, 0.009 mmol). The reaction mixture was heated at 110° C. for 18 h and cooled, and 1 M aqueous NH4Cl was added. The mixture was extracted with portions of ethyl ether. The combined organic phase was dried over anhydrous MgSO4 and concentrated under diminished pressure to afford a crude residue. Elution with ethyl acetate gave 4-(benzyloxy)-3-heptyl-5-methoxy-2,6-dimethylpyridine (20) as a light yellow oil: yield 19 mg (71%); silica gel TLC Rf 0.3 (1:1 hexane/ethyl acetate); 1H NMR (CDCl3) δ 0.60-0.89 (m, 3H), 1.26-1.30 (m, 10H), 2.48 (s, 3H), 2.60-2.62 (m, 2H) 2.74 (s, 3H), 3.70 (s, 3H), 4.95 (s, 2H), 7.38-7.42 (m, 4H) and 7.53-7.56 (m, 1H).

Quelle