反応 #48809

反応方程式

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

iodotrimethylsilane

potassium carbonate

sodium thiosulphate

→

desired compound

収率 74.4%

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

収率 74.4%

溶媒

acetonitrile

Methanol

反応条件

後処理

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

実験手順

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).

出典