Dimethyl Sulfate → Methyl 2-methoxy-3-(3-nitrophenyl)prop-2-enoate

HRID 2370474Notes

Reaction equation

HRID 2370474 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[OH:8][C:9](=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)[C:10](O)=[O:11].[C:23](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:23][O:8][C:9](=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)[C:10]([O:6][CH3:7])=[O:11]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 10796Cesium carbonateHCID 66905811HCID 66905811, compound

Product 1

HCID 66905787Methyl 2-methoxy-3-(3-nitrophenyl)prop-2-enoateYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethyl sulfate (13.23 g, 105 mmol) was added to a stirred mixture of 2-hydroxy-3-(3-nitrophenyl)acrylic acid (10.5 g, 50.0 mmol) and caesium carbonate (39.1 g, 120 mmol) in DMF (105 ml) to form a clear, pale yellow mixture, which was stirred at RT overnight. The resulting dark red suspension was concentrated in vacuo and the residue partitioned between water (100 ml) and dichloromethane (150 ml). The organic layer was separated, further washed with water (2×100 ml), dried over sodium sulphate and filtered through silica gel. The resulting yellow solution was evaporated to dryness in vacuo to give methyl 2-methoxy-3-(3-nitrophenyl)acrylate as a yellow solid (8.1 g, 67%). 1H NMR (δ, 250 MHz, DMSO-d6)=3.81 (3H, s), 3.83 (3H, s), 7.08 (1H, s), 7.71 (1H, dd, 7.9 & 8.2 Hz), 8.10-8.22 (2H, m), 8.66 (1H, s).

Workup

  1. customto form a clear, pale yellow mixture, which
  2. concentrationThe resulting dark red suspension was concentrated in vacuo
  3. customthe residue partitioned between water (100 ml) and dichloromethane (150 ml)
  4. customThe organic layer was separated
  5. washfurther washed with water (2×100 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered through silica gel
  8. customThe resulting yellow solution was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-3073baac63bd45ed950f7707ca3e848b
Source dataset
uspto-grants-2014_04
Patent number
US08710100B2

Reaction notes

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