Réaction #531905

Équation de réaction

4-fluoro phenyl acetic acid

3,4,5 trimethoxybenzaldehyde

Ac2O

DIPEA

HCl

→

product

Rendement 56.0%

3-(3,4,5-trimethoxyphenyl)-2-(4-fluorophenyl)acrylic acid

Rendement 56.0%

Solvants

DCM MeOH

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   Autrethe precipitate formed
3. 3
   Filtrationwas filtered
4. 4
   workup.DISSOLUTIONdissolved in DCM (100 mL)
5. 5
   LavageThe organic layer was washed with 10% aqueous NaOH (3×50 mL)
6. 6
   AutreThe precipitate formed
7. 7
   Filtrationwas filtered
8. 8
   Lavagewashed with 100 mL water
9. 9
   Autredried

Mode opératoire

A mixture of 4-fluoro phenyl acetic acid (2 g, 13 mmol), 3,4,5 trimethoxybenzaldehyde (2.5 g, 13 mmol), Ac2O (10 mL) and DIPEA (2.9 mL, 16.8 mmol) was stirred at room temperature for 12 hours. Upon completion, as monitored by TLC using DCM:MeOH (9:1) as the eluent, 10% aqueous HCl (10 mL) was added to the reaction mixture; the precipitate formed was filtered and dissolved in DCM (100 mL). The organic layer was washed with 10% aqueous NaOH (3×50 mL) and the basic aqueous solution was acidified with 10% aqueous HCl to pH 3. The precipitate formed was filtered, washed with 100 mL water and dried to get the product (2.4 g, 56% yield).

Source