Dimethyl Sulfoxide → Ethyl 5-methyl-3-(nitromethyl)hexanoate

HRID 1034564Notes

Reaction equation

HRID 1034564 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].C1CCN2C(=NCCC2)CC1.CS(C)=O.[CH2:20]([O:22][C:23](=[O:30])[CH:24]=[CH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH3:21]>C(Cl)Cl>[CH2:20]([O:22][C:23](=[O:30])[CH2:24][CH:25]([CH2:4][N+:1]([O-:3])=[O:2])[CH2:26][CH:27]([CH3:29])[CH3:28])[CH3:21]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1022442-Hexenoic acid, 5-methyl-, ethyl ester

Product 1

HCID 14463328Ethyl 5-methyl-3-(nitromethyl)hexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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%).

Workup

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

Sources & evidence

ORD record
ord-815fdcff00f843899f38a36da582ff51
Source dataset
uspto-grants-2013_10
Patent number
US08546112B2

Reaction notes

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