Reaktion #48976

Reaktionsgleichung

Sodium ethoxide

methyl 3-(2,3-bis(cyclopentyloxy)-4-methoxyphenyl)-3-oxopropanoate

((2-bromoethoxy)methyl)benzene

→

ethyl 4-(benzyloxy)-2-(2,3-bis(cyclopentyloxy)-4-methoxybenzoyl)butanoate

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter refluxing for 1 h
2. 2
   Temperaturrefluxing
3. 3
   Einengenconcentrated
4. 4
   workup.ADDITIONdiluted with ethyl acetate (300 mL)
5. 5
   Waschenwashed with brine (50 mL×2)
6. 6
   SonstigeThe organic layer was dried
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   Sonstigepurified by silica gel chromatography (ethyl acetate:petroleum ether)

Vorschrift

Sodium ethoxide (2.0 g, 29 mmol) was added to a solution of methyl 3-(2,3-bis(cyclopentyloxy)-4-methoxyphenyl)-3-oxopropanoate (11 g, 29 mmol) and ethanol (150 mL) at rt. After refluxing for 1 h, ((2-bromoethoxy)methyl)benzene (12.5 g, 57.8 mmol) was added and refluxing was continued overnight. The reaction was allowed to cool to rt, concentrated, diluted with ethyl acetate (300 mL), and then washed with brine (50 mL×2). The organic layer was dried, filtered, concentrated, and purified by silica gel chromatography (ethyl acetate:petroleum ether) to give ethyl 4-(benzyloxy)-2-(2,3-bis(cyclopentyloxy)-4-methoxybenzoyl)butanoate: MS (ESI): 525.

Quelle