Sodium hydride → 6-Bromo-3-benzofuranacetonitrile

Reaktionsgleichung

[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[Br:14][C:15]1[CH:24]=[CH:23][C:18]2[C:19](=O)[CH2:20][O:21][C:17]=2[CH:16]=1>C1COCC1>[Br:14][C:15]1[CH:24]=[CH:23][C:18]2[C:19]([CH2:5][C:3]#[N:4])=[CH:20][O:21][C:17]=2[CH:16]=1

Komponenten

Versuchsvorschrift

Sodium hydride (0.7 g, 0.0173 mol) was washed with hexanes then suspended in THF (8 mL). Diethyl cyanomethylphosphonate (3.07 g, 0.0173 mol) was added dropwise and stirred 10 minutes to give clear yellow solution. A solution of 11-5 (3.38 g, 0.0158 mol) in THF (20 mL) was added dropwise, the solution stirred for 0.5 hour, then heated to reflux for 0.5 hour. A solution of 6N HCL (3.4 mL) was added and the THF was removed under vacuum. The concentrated solution was diluted with Et2O and washed with 4×30 mL 6N HCl, the ether layer was dried (MgSO4), filtered and evaporated. The residue was chromatographed (20% EtOAc/Hexanes) to give 11-6 as an orange solid.