Reaktion #531905

Reaktionsgleichung

4-fluoro phenyl acetic acid

3,4,5 trimethoxybenzaldehyde

Ac2O

DIPEA

HCl

→

product

Ausbeute 56.0%

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

Ausbeute 56.0%

Lösungsmittel

DCM MeOH

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle