Nitromethane → Methyl 3-(4,4-difluorocyclohexyl)-4-nitrobutanoate

Participants

Reaction Steps

Methyl 3-(4,4-difluorocyclohexyl)prop-2-enoate (4.054 g, 0.198 mol, 1 eq) is dissolved in nitromethane (23 L, 0.423 mol, 21.3 eq) and 1,8-diazabicyclo[5,4,0]undec-7-ene (3.025 g, 0.198 mol, 1 eq) is added at room temperature. The solution is stirred overnight at room temperature then evaporated. The residue is dissolved in ethyl acetate and the solution is washed with 1 M HCl and water. The organic phase is dried with MgSO4 and evaporated under vacuum. The residue is purified by chromatography over silicagel (eluent: CH2Cl2 100%) to afford methyl 3-(4,4-difluorocyclohexyl)-4-nitrobutanoate a1-20.

Provenance & Evidence