Methyl iodide → Methyl 3-methoxy-2-phenyl-2-propenoate

HRID 440381

Reaction equation

HRID 440381 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:14]([O:16][CH3:17])=O.CI>CN(C)C=O.O.CO.O1CCCC1.CCCCCC>[CH3:14][O:16][CH:17]=[C:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

10

Reactant 4

HCID 6328Methyl iodideHCID 7559Methyl phenylacetateHCID 7865Methyl formateHCID 24758Sodium hydride

Product 1

HCID 331481Methyl 3-methoxy-2-phenyl-2-propenoate

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

Combine hexane washed sodium hydride (24 g, 60% in oil, 580 mmol) and tetrahydrofuran (400mL). Cool to about 5° C. Simultaneously, add dropwise methyl phenylacetate (40 g, 270 mmol) and the methyl formate (35 g, 580 mmol). Add methanol (0.5 mL). Warm to ambient temperature. After 18 hours, pass nitrogen gas over the reaction mixture to remove the solvent to give a residue. Dissolve the residue in dimethylformamide (400 mL) and cool to about 5° C. Slowly add methyl iodide (76 g, 540 mmol). After the addition is complete, warm to ambient temperature. After 3 hours, pour the reaction mixture into water and extract 2 times with diethyl ether. Extract the combined organic layers 5 times with water and once with aqueous saturated sodium chloride solution. Dry the organic layer over MgSO4 and evaporate in vacuo to give the title compound.

Workup

  1. temperatureWarm to ambient temperature
  2. customto remove the solvent
  3. customto give a residue
  4. temperaturecool to about 5° C
  5. additionAfter the addition
  6. temperaturewarm to ambient temperature
  7. waitAfter 3 hours
  8. extractionextract 2 times with diethyl ether
  9. extractionExtract the combined organic layers 5 times with water
  10. dry with materialDry the organic layer over MgSO4
  11. customevaporate in vacuo

Sources & evidence

ORD record
ord-9cc24f3b45b642ba994e435728f5e63b
Source dataset
uspto-grants-1996_05
Patent number
US05519048

Linked notes

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