Reaction #7934

Reaction equation

4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

tributyl-(4-methoxymethoxy-phenyl)-stannane

→

9a-butyl-7-methoxy-4-(4-methoxymethoxy-phenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Yield 84.5%

Solvents

toluene

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperaturethe mixture was cooled to room temperature
3. 3
   Otherevaporated under vacuum to a dark oil (2.208 g)
4. 4
   OtherThis material was purified by chromatography on EM silica gel 60 (230-400 mesh, 115 mL dry)
5. 5
   Washas eluting solvent

Procedure

A mixture of 4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (800 mg, 2.29 mmol), Pd(PPh3)4 (132 mg, 0.114 mmol), and tributyl-(4-methoxymethoxy-phenyl)-stannane (1.174 g, 2.75 mmol) in anhydrous toluene (11.5 mL) was placed under a nitrogen atmosphere and heated with stirring in an oil bath at 100° C. After 22 hours, the mixture was cooled to room temperature and evaporated under vacuum to a dark oil (2.208 g). This material was purified by chromatography on EM silica gel 60 (230-400 mesh, 115 mL dry), using 4:1 hexanes-EtOAc as eluting solvent, to afford 9a-butyl-7-methoxy-4-(4-methoxymethoxy-phenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (787 mg) as a yellow gum.

Source