Reaktion #9786

Reaktionsgleichung

2-fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile

intermediate 101

2-fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile

hydrochloric acid

→

(4-{2-[5-(4-cyano-3-fluorophenyl)-3-methylthien-2-yl]ethyl}-2-methylphenoxy)acetic acid

Lösungsmittel

2-propanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 2 hours
2. 2
   SonstigeThe solvent was removed
3. 3
   workup.DISSOLUTIONthe residue dissolved in 1,4-dioxane (2 ml)
4. 4
   workup.ADDITIONThis mixture was treated with 2M aqueous sodium hydroxide (0.5 ml)
5. 5
   workup.STIRRINGthe mixture stirred for 16 hours)
6. 6
   SonstigeThe solvent was removed
7. 7
   Sonstigethe residue purified by SPE (aminopropyl)
8. 8
   SonstigeThe title compound, as the free acid, was recovered
9. 9
   workup.ADDITIONby treating a solution of this product with Dowex H+

Vorschrift

A mixture of 2-fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile (intermediate 101, 0.016 g) in 2-propanol (2 ml) was treated with 2M aqueous hydrochloric acid (1 ml) and the mixture stirred at reflux for 2 hours. The solvent was removed and the residue dissolved in 1,4-dioxane (2 ml) and water (1 ml). This mixture was treated with 2M aqueous sodium hydroxide (0.5 ml) and the mixture stirred for 16 hours). The solvent was removed and the residue purified by SPE (aminopropyl). The title compound, as the free acid, was recovered by treating a solution of this product with Dowex H+.

Quelle