Reaktion #48809

Reaktionsgleichung

3-hydroxy-5-[(1S)-2-methoxy-(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

iodotrimethylsilane

potassium carbonate

sodium thiosulphate

→

desired compound

Ausbeute 74.4%

3-Hydroxy-5-{[(S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Ausbeute 74.4%

Lösungsmittel

acetonitrile

Methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred for 2 hours
2. 2
   SonstigeThe acetonitrile was removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue dissolved in water (150 mL)
4. 4
   Extraktioncontinuously extracted with ethyl acetate for 16 hours
5. 5
   SonstigeThe ethyl acetate was removed in vacuo
6. 6
   Sonstigethe residue chromatographed on silica (eluting with 0-5% methanol in ethyl acetate)

Vorschrift

To a solution of 3-hydroxy-5-[(1S)-2-methoxy-(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (10.0 g) in acetonitrile (200 mL), under an atmosphere of argon, was added iodotrimethylsilane (23.8 mL) and the resultant mixture stirred for 16 hours. Methanol (30 mL) was then added and the mixture stirred for 15 minutes, saturated potassium carbonate (30 mL) and sodium thiosulphate (0.5 g) were then added and the mixture stirred for 2 hours. The acetonitrile was removed in vacuo, the residue dissolved in water (150 mL) and continuously extracted with ethyl acetate for 16 hours. The ethyl acetate was removed in vacuo and the residue chromatographed on silica (eluting with 0-5% methanol in ethyl acetate) to give the desired compound (7.1 g).

Quelle