Ethyl Acetate → HCID 14835684, compound

HRID 1709247Notes

Reaction equation

HRID 1709247 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28].C(OCC)(=O)C>O1CCCC1.O>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22](/[CH:23]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 7006084-Methoxy-3-nitrobenzaldehyde

Product 1

HCID 14835684HCID 14835684, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2.40 g of sodium hydride (purity: 60%) was suspended in 60 ml of tetrahydrofuran. To the suspension was dropwise added 13.5 g of ethyl diethylphosphonoacetate with ice-cooling. The mixture was stirred for 30 minutes at room temperature. To the resulting reaction mixture was dropwise added a solution of 9.06 g of 4-methoxy-3-nitrobenzaldehyde dissolved in 30 ml of tetrahydrofuran, with ice-cooling. The mixture was stirred for 30 minutes at the same temperature. To the reaction mixture was added 100 ml of ethyl acetate and 50 ml of water, and the organic layer was separated. The organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain ethyl (E)-3-(4-methoxy-3-nitrophenyl)acrylate.

Workup

  1. temperaturecooling
  2. customTo the resulting reaction mixture
  3. temperaturecooling
  4. stirringThe mixture was stirred for 30 minutes at the same temperature
  5. customthe organic layer was separated
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-3f1cc50f97de4be498110be8054208d6
Source dataset
uspto-grants-1990_08
Patent number
US04948796

Reaction notes

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