Carbon Dioxide → HCID 21685535, compound

Participants

Reaction Steps

1,1-dibromo-2-(tert-butyldimethylsilyloxyphenyl)ethylene (190.9 mg, 0.487 mmol) prepared in 2) was dissolved in tetrahydrofuran (2.9 ml) in nitrogen atmosphere, and a 1.58 mol/l n-butyllithium/hexane solution (832 μl, 1.31 mmol) was dropwise added at −78° C. After stirring for one hour, crushed dry ice was added to return the solution to 0° C. After stirring for 10 minutes, water was added, and the solution was concentrated under reduced pressure. The residue was diluted with diethyl ether and extracted with water. The obtained aqueous layer was acidified (pH=4) with a saturated potassium hydrogen sulfate aqueous solution and extracted with ethyl acetate. The obtained organic layer was washed with a saturated salt solution, dried over anhydrous sodium sulfate, subjected to filtration and concentrated under reduced pressure to give 3-(4-tert-butyldimethylsilyloxyphenyl)propionic acid (134.6 mg, quant.) as crude crystals.

Provenance & Evidence