反応 #607435

反応方程式

(2Z)-(hydroxyimino)(phenyl)acetonitrile

2-bromo-4-(bromomethyl)thiazole

potassium iodide

caesium carbonate

→

(2Z)-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile

収率 88.0%

溶媒

DMF

acetonitrile

反応条件

後処理

1. 1
   その他The solvent was then evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in EtOAc
3. 3
   洗浄subsequently washed with H2O and brine
4. 4
   その他Ater separation
5. 5
   乾燥the organic phase was dried over MgSO4
6. 6
   濃縮then concentrated
7. 7
   その他The residue was purified by chromatography on silica gel

実験手順

To a mixture of (2Z)-(hydroxyimino)(phenyl)acetonitrile (2.9 g, 19.84 mmol, 1 eq.), 2-bromo-4-(bromomethyl)thiazole (5.10 g, 19.84 mmol, 1 eq.), potassium iodide (329 mg, 1.98 mmol, 0.1 eq.) and caesium carbonate (9.70 g, 29.76 mmol, 1.5 eq.) was added 80 ml of acetonitrile and 10 ml of DMF. The reaction was stirred 2 h at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc, subsequently washed with H2O and brine. Ater separation, the organic phase was dried over MgSO4 then concentrated. The residue was purified by chromatography on silica gel to give (2Z)-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (5.70 g, 88% yield, only 1 oxime isomer).

出典