反応 #1778205

反応方程式

5-p-tolyloxy-thiophene-2-carbonitrile

diisobutyl aluminum hydride

tetrahydrofuran

→

title compound

収率 47.2%

5-p-Tolyloxy-thiophene-2-carbaldehyde

収率 47.2%

反応条件

後処理

1. 1
   温度The reaction mixture was cooled to room temperature
2. 2
   抽出extracted with ethyl acetate
3. 3
   workup.ADDITIONafter addition of water
4. 4
   洗浄The organic layer was washed with saturated aqueous sodium chloride
5. 5
   その他the solvent was evaporated under a reduced pressure
6. 6
   その他The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5)

実験手順

To a tetrahydrofuran (70.0 mL) solution of 5-p-tolyloxy-thiophene-2-carbonitrile (2.00 g, 9.29. mmol) described in Manufacturing Example 48-1-1 was added dropwise diisobutyl aluminum hydride (0.97 M n-hexane solution, 23.9 mL, 23.2 mmol) on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere, which was stirred for 3 hours at room temperature. The reaction mixture was cooled to room temperature and extracted with ethyl acetate after addition of water. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5) to obtain the title compound (958 mg, 47.2%).

出典