反応 #747991

反応方程式

3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde

3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde

2-pyridyl magnesium bromide

→

title compound

5-[2-Benzyloxy-4-(hydroxypyridin-2-yl-methyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

溶媒

THF

反応条件

後処理

1. 1
   その他is quenched with saturated NH4Cl
2. 2
   抽出The mixture is extracted with EtOAc
3. 3
   乾燥the organic phase is dried over MgSO4
4. 4
   その他The solvent is removed under reduced pressure
5. 5
   その他the crude material is purified by column chromatography

実験手順

To a solution of 3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde (Example 81, step B) (75 mg, 0.17 mmol) in anhydrous THF (4 mL) at −78° C. is added dropwise 2-pyridyl magnesium bromide (0.25M in THF, 1.36 mL, 0.34 mmol). The reaction is stirred at −78° C. for 1 h, then is quenched with saturated NH4Cl. The mixture is extracted with EtOAc and the organic phase is dried over MgSO4. The solvent is removed under reduced pressure and the crude material is purified by column chromatography using a gradient of 0-50% EtOAc/hexane to afford the title compound as a colorless oil: (M−H)−=526.

出典