Reaktion #6471

Reaktionsgleichung

acetic acid

3-benzyloxyacetophenone

methyl 3-formylbenzoate

CH3ONa

→

1-(3-Benzyloxyphenyl)-3-(3-(methoxycarbonyl)phenyl)-2-propen-1-one

Lösungsmittel

CH3OH

H2O

CH3OH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA heavy precipitate formed almost immediately
2. 2
   FiltrationTitle product was recovered by filtration, air
3. 3
   Sonstigedried
4. 4
   Sonstigepurified by chromatography on silica gel
5. 5
   Waschengradiently eluted with 49 to 39:1 toluene

Vorschrift

To CH3ONa (0.45 g, 0.0082 mol) stirring in 20 ml of dry CH3OH at 10° C. was added 3-benzyloxyacetophenone (5.0 g, 0.019 mol) and methyl 3-formylbenzoate (3.12 g, 0.019 mol). A heavy precipitate formed almost immediately, and the mixture was diluted with 20 ml CH3OH, warmed to room temperature and stirred for 18 hours. Glacial acetic acid (3 ml) was added and the mixture poured into 300 ml H2O. Title product was recovered by filtration, air dried and purified by chromatography on silica gel gradiently eluted with 49 to 39:1 toluene:ethyl acetate, 4.97 g of solid; MS 372.2 (M+); 1H-NMR (300 MHz, CDCl3) delta (ppm) 3.95 (s, 3H), 5.14 (s, 2H), 7.2-7.9 (m, 13H), 8.06 (dt, 1H), 8.3 (s, 1H); TLC Rf 0.7 (49:1 CHCl3 :isopropanol).

Quelle