Reaction #1121746

Reaction equation

nitromethane

DBU

DMSO

α,β-unsaturated ester

5-methyl-hex-2-enoic acid ethyl ester

→

γ-nitroester

5-methyl-3-nitromethyl-hexanoic acid ethyl ester

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Washthe resulting mixture was washed with 2×20 mL of 1M aqueous H2SO4 and 1×20 mL of 0.5M aqueous NaHCO3
2. 2
   OtherThe organic layer was dried
3. 3
   Otherthe solvent was removed under reduced pressure

Procedure

7.0 g of nitromethane and 3.3 mL of DBU (1,8-diazabicyclo[5.4.0]undece-7-en) were added to the DMSO solution of α,β-unsaturated ester VII. The reaction mixture was stirred until complete conversion was detected by GC. 20 mL of CH2Cl2 were added and the resulting mixture was washed with 2×20 mL of 1M aqueous H2SO4 and 1×20 mL of 0.5M aqueous NaHCO3. The organic layer was dried and the solvent was removed under reduced pressure. 3.6 g of γ-nitroester VIII were obtained (yield over two steps: 75%).

Source