Reaktion #361598

Reaktionsgleichung

LiH

HMPA

3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl ester

2-methyl-2-propanethiol

→

title compound

3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoic acid

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was slowly heated to 150° C.
2. 2
   workup.WAITkept at that temperature for 18 hours
3. 3
   TemperaturAfter cooling to room temperature
4. 4
   Sonstigethe supernatant layer was decanted
5. 5
   workup.DISSOLUTIONthe residue dissolved in H2O
6. 6
   Extraktionacidifed with 1N HCl, extracted twice with Et2O
7. 7
   Waschenwashed twice with brine
8. 8
   Trocknendried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated to dryness

Vorschrift

To a mixture of LiH (12.6 g) and HMPA (105 mL) in DMF (1050 mL) at 0° C. was added 2-methyl-2-propanethiol (178 mL). The mixture was stirred at room temperature for 30 min, then 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl ester (150 g) (EP 419,049, Example 1, Step A) in DMF (450 mL) was added slowly. The mixture was slowly heated to 150° C. and kept at that temperature for 18 hours. After cooling to room temperature, the supernatant layer was decanted and the residue dissolved in H2O and acidifed with 1N HCl, extracted twice with Et2O, washed twice with brine, dried over MgSO4, filtered and evaporated to dryness to provide the title compound.

Quelle