Reaction #2446098

Reaction equation

HCl

2,8-di-(triphenylsilyl)-dibenzofuran

DMF

→

2,8-di-(triphenylsilyl)-dibenzofuran-4-carboxaldehyde

Yield 30.2%

Solvents

THF

cyclohexane

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction mixture is stirred for 1 h
2. 2
   Otherto quench
3. 3
   Otherthe reaction
4. 4
   ExtractionThe product is extracted with ethylacetate
5. 5
   Otherpurified by column chromatography on silica gel with heptane:ethylacetate (3:1) as an eluent

Procedure

1 g (1.46 mmol) 2,8-di-(triphenylsilyl)-dibenzofuran are dissolved in 100 ml dry THF at 45° C. and 10 ml of 1.4 M sec-Buthyllithium solution in cyclohexane is added. After stirring for 15 min. at 45° C., 2 ml of dry DMF is added; the reaction mixture is stirred for 1 h. 100 ml of 0.5 M HCl is added to quench the reaction. The product is extracted with ethylacetate and purified by column chromatography on silica gel with heptane:ethylacetate (3:1) as an eluent. 2,8-di-(triphenylsilyl)-dibenzofuran-4-carboxaldehyde (5.3) is obtained in 30.2% yield.

Source