Réaction #165098

Équation de réaction

5-p-tolyloxy-thiophene-2-carbonitrile

diisobutyl aluminum hydride

tetrahydrofuran

→

title compound

Rendement 47.2%

5-p-Tolyloxy-thiophene-2-carbaldehyde

Rendement 47.2%

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to room temperature
2. 2
   Extractionextracted with ethyl acetate
3. 3
   workup.ADDITIONafter addition of water
4. 4
   LavageThe organic layer was washed with saturated aqueous sodium chloride
5. 5
   Autrethe solvent was evaporated under a reduced pressure
6. 6
   AutreThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5)

Mode opératoire

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%).

Source