Reaction #2006422

Reaction equation

3-carboxybenzaldehyde

lithium bis(trimethylsilyl)amide

lithium bis(trimethylsilyl) amide

benzyltriphenylphosphonium bromide

HCl

→

title compound

Yield 17.6%

3-(2-Phenylethenyl)-benzoic Acid

Yield 17.6%

Solvents

THF

THF

THF

ethyl acetate

Conditions

Workup

1. 1
   Extractionthe separated aqueous layer was extracted with ethyl acetate (3×50 mL)
2. 2
   Dryingdried (MgSO4 anh.)
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated
5. 5
   OtherThe residue was purified by HPLC (10:95 CH3CN:H2O, TFA 0.1%)

Procedure

A 1.0 M solution of lithium bis(trimethylsilyl) amide (3.3 mL, 3.3 mmol) in THF was added to a stirred suspension of benzyltriphenylphosphonium bromide (1.44 g, 3.6 mmol) in THF (35 mL) at 0° C. The resulting orange solution was added via cannula to a mixture of 3-carboxybenzaldehyde (500 mg, 3.3 mmol) and lithium bis(trimethylsilyl)amide (3.3 mL, 3.3 mmol) in THF (10 mL). The mixture was stirred overnight at room temperature. A 1N solution of HCl (75 mL) and ethyl acetate (75 mL) were added and the separated aqueous layer was extracted with ethyl acetate (3×50 mL), dried (MgSO4 anh.) filtered and evaporated. The residue was purified by HPLC (10:95 CH3CN:H2O, TFA 0.1%) to afford 130 mg of the title compound (17%).

Source