Reaction #44505

Reaction equation

solution

tert-butyl-(cyclohept-4-enyloxy)-diphenyl-silane

ethyl diazoacetate

→

title compound

4-(tert-butyl-diphenyl-silanyloxy)-bicyclo[5.1.0]octane-8-carboxylic acid ethyl ester

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   OtherThe solvent was evaporated in vacuo and product
2. 2
   Otherpurified by flash column chromatography (hexanes:ethyl acetate 100:0 to 80:20)

Procedure

To a solution of Example 8C (2.2 g, 6.28 mmoles) and Rh2(OAc)4 (2 mg, 4.3 μmol) in dichloromethane (2 mL), ethyl diazoacetate (0.717 g, 6.28 mmoles) in dichloromethane (4 mL) was added over two hours via a syringe pump. The solvent was evaporated in vacuo and product purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 80:20) to provide the title compound.

Source