反应详情

温度

135 °C

A mixture of 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (11.5 g, 39.0 mmol), prepared in the previous step, and zinc cyanide (2.7 g, 23.5 mmol) in dry dimethylformamide (100 mL) was degassed and put under a nitrogen atmosphere. Tetrakis(triphenylphosphine)palladium(0) (1.7 g, 1.5 mmol) was added and the mixture again degassed and put under a nitrogen atmosphere. The mixture was stirred at 135° C. overnight. An additional 171 mg of tetrakis(triphenylphosphine)palladium(0) was added and the reaction stirred for another 4 h. The reaction mixture was filtered through the Celite™ reagent and rinsed with ethyl acetate. The filtrate was washed with water. The layers were separated and the organic layer was dried over anhydrous sodium sulfate. The organic layer was filtered and concentrated in vacuo to give 8.1 g of crude product. Purification of the crude product on silica gel using a step-wise gradient of 5% to 15% ethyl acetate: hexane as the eluent gave 5-oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile (2.8 g, 41%), MS(ES) m/z 172 [M+H]+.

1. customwas degassed
2. customthe mixture again degassed
3. additionAn additional 171 mg of tetrakis(triphenylphosphine)palladium(0) was added
4. stirringthe reaction stirred for another 4 h
5. filtrationThe reaction mixture was filtered through the Celite™ reagent
6. washrinsed with ethyl acetate
7. washThe filtrate was washed with water
8. customThe layers were separated
9. dry with materialthe organic layer was dried over anhydrous sodium sulfate
10. filtrationThe organic layer was filtered
11. concentrationconcentrated in vacuo
12. customto give 8.1 g of crude product
13. customPurification of the crude product on silica gel using a step-wise gradient of 5% to 15% ethyl acetate