Nitromethane → Ethyl 3-(4-chlorophenyl)-4-nitrobutanoate

HRID 1402839

Reaction equation

HRID 1402839 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.CN(C)C(N(C)C)=N.[N+:23]([CH3:26])([O-:25])=[O:24]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([CH2:26][N+:23]([O-:25])=[O:24])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 2014712-Propenoic acid, 3-(4-chlorophenyl)-, ethyl ester

Product 1

HCID 11097654Ethyl 3-(4-chlorophenyl)-4-nitrobutanoateYield 92.9%

Procedure

The solution of ethyl 4-chlorocinnamate (12.6 g) and N,N,N′,N′-tetramethylguanidine (1.2 g) in nitromethane (36.6 g) was kept at rt for three days. The excess of nitromethane was evaporated and the residue dissolved in diethyl ether (250 ml). The organic layer was washed with 2M HCl (2×150 ml), dried (sodium sulfate), and evaporated. The residue was subjected to purification by flash chromatography on silica gel (petrol ether/ethyl acetate 10:1) to give ethyl 3-(4-chlorophenyl)-4-nitrobutanoate (15.1 g) as yellowish oil.

Workup

  1. customThe excess of nitromethane was evaporated
  2. dissolutionthe residue dissolved in diethyl ether (250 ml)
  3. washThe organic layer was washed with 2M HCl (2×150 ml)
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customThe residue was subjected to purification by flash chromatography on silica gel (petrol ether/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-5c511d6b0d524f17a4214faf2eba502b
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Linked notes

Loading…