Hydrochloric Acid → Ethyl 3-(2-nitrophenyl)prop-2-enoate

HRID 2223849Notes

Reaction equation

HRID 2223849 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[N+:17]([C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O)([O-:19])=[O:18].Cl>O1CCCC1.O>[N+:17]([C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([O-:19])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride

Product 1

HCID 235998Ethyl 3-(2-nitrophenyl)prop-2-enoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 60% sodium hydride/mineral oil (1.11 g) in tetrahydrofuran (40 mL) was added ethyl diethylphosphonoacetate (6.29 mL) dropwise under ice cooling. After stirring the mixture under ice cooling for 30 minutes, a solution of 2-nitrobenzaldehyde (3.0 g) in tetrahydrofuran (30 mL) was added thereto under ice cooling. The solution was stirred at room temperature for 8 hours. Water and 3N hydrochloric acid were then added to the solution and it was extracted with diethyl ether. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=3:2) to give the title compound (3.74 g).

Workup

  1. stirringThe solution was stirred at room temperature for 8 hours
  2. extractionwas extracted with diethyl ether
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-eaabd66827a44f40a8b2ddc20faeabc5
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

Loading…