反应详情

温度

80 °C

To a stirred solution of triisopropylsilanethiol (Tetrahedron Lett. 1994, 35, 3221.; 684 mg, 3.6 mmol) in toluene (5 ml) was added sodium hydride (60% oil dispersion, 144 mg, 3.6 mmol) under a nitrogen atmosphere. After stirring for 15 min, the resulting solution was added to a mixture of (2SR, 4RS)-4-cyano-4-(3-iodophenyl)-2-methyl-3,4,5,6-tetrahydro-2H-pyran (1.07 g, 3.27 mmol) and tetrakis(triphenylphosphine)palladium(0) (114 mg, 0.1 mmol) in toluene (20 ml), and the mixture was heated at 80° C. for 1 h. The resulting mixture was cooled, poured into water (50 ml) and extracted with Et2O (100 ml). The organic extract was washed with water (50 ml), brine (50 ml), dried (MgSO4) and concentrated. Purification by silica gel column chromatography, eluting with ethyl acetate-hexane (1:9), gave 1.23 g (96%) of the titled compound as a red oil.

1. temperatureThe resulting mixture was cooled
2. extractionextracted with Et2O (100 ml)
3. extractionThe organic extract
4. washwas washed with water (50 ml), brine (50 ml)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customPurification by silica gel column chromatography
8. washeluting with ethyl acetate-hexane (1:9)