tert-Butanol → 3-Amino-3-(4-chlorophenyl)-2-methyl-2-propenenitrile

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Reaction Steps

In a 2 L round bottom flask (fitted with rubber septum, nitrogen blanket and stir bar) combine 4-chlorobenzonitrile (60.0 g, 1.00 equiv, 432 mmol), propionitrile (61.2 mL, 2.00 equiv, 864 mmol), tetrahydrofuran (43.2 mL) and 1.0 M potassium t-butoxide in t-butanol (tert-butyl alcohol, potassium derivative, 475 mL, 1.10 equiv; 475 mmol); and stir for 24 h. Quench with aqueous NaHCO3 and extract with ethyl acetate. Wash the organic phase 2 times with brine, dry (K2CO3), filter, and concentrate to dryness. Purify by flash chromatography on silica, eluting with 15:85 to 50:50 ethyl acetate/hexane, to afford 3-amino-3-(4-chlorophenyl)-2-methylacrylonitrile (as an uncharacterized E-/Z-mixture). Yield: 49.5%. LCMS: 193.0 (m+1).

Provenance & Evidence