Réaction #4840

Équation de réaction

ether

methyl 3-bromo-3-methyl-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}propanoate

tetrahydrofuran

→

3-methyl-3-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-propenoic acid

Conditions de réaction

Traitement

1. 1
   AutreThe resulting reaction mixture
2. 2
   Autrethe reaction
3. 3
   AutreThe solvent can be removed
4. 4
   workup.DISSOLUTIONthe residual oil dissolved in ether
5. 5
   Autreto obtain an ether solution which
6. 6
   Extractioncan be extracted with 1N hydrochloride acid
7. 7
   TempératureThe resulting sodium hydroxide solution can be heated on the steam bath
8. 8
   Températurecooled
9. 9
   Autreto obtain a product which
10. 10
    SéchageThe resulting ether solution can be dried with anhydrous magnesium sulfate
11. 11
    Filtrationfiltered
12. 12
    Autreevaporated

Mode opératoire

To a solution of methyl 3-bromo-3-methyl-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}propanoate in tetrahydrofuran can be added an equivalent amount of 1,5-diazabicyclo[3.4.0]nonene-5. The resulting reaction mixture can be stirred at elevated temperature until thin layer chromatographic analysis of a reaction sample indicates the reaction to be complete. The solvent can be removed and the residual oil dissolved in ether to obtain an ether solution which can be extracted with 1N hydrochloride acid and then by 2N sodium hydroxide solution. The resulting sodium hydroxide solution can be heated on the steam bath, cooled and made acidic with concentrated hydrochloric acid to obtain a product which can be isolated from the aqueous phase with ether. The resulting ether solution can be dried with anhydrous magnesium sulfate, filtered, and evaporated to give 3-methyl-3-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-propenoic acid.

Source