Reaction #48976

Reaction equation

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

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureAfter refluxing for 1 h
2. 2
   Temperaturerefluxing
3. 3
   Concentrationconcentrated
4. 4
   workup.ADDITIONdiluted with ethyl acetate (300 mL)
5. 5
   Washwashed with brine (50 mL×2)
6. 6
   OtherThe organic layer was dried
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   Otherpurified by silica gel chromatography (ethyl acetate:petroleum ether)

Procedure

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.

Source