Methyl iodide → HCID 85401425, compound

HRID 582053Notes

Reaction equation

HRID 582053 reaction equation
C[O-].[Na+].[CH:4]([O:6][CH3:7])=[O:5].[N+:8]([C:11]1[CH:12]=[C:13]([CH2:17][C:18]([O:20][CH3:21])=O)[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9].CI>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[CH3:21][O:20][CH:18]=[C:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 7865Methyl formateHCID 526967Methyl 2-(3-nitrophenyl)acetateHCID 10942334Sodium Methoxide

Product 1

HCID 85401425HCID 85401425, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Combine freshly prepared sodium methoxide (9.3 g, 172 mmol) and tetrahydrofuran (125 mL). Cool to 0° C. Add methyl formate (10.6 mL, 172 mmol). Add dropwise a solution of methyl (3-nitrophenyl)acetate (15.3 g, 78.3 mmol) in tetrahydrofuran (125 mL). After the addition is complete, warm the reaction mixture to ambient temperature. After 16 hours, evaporate in vacuo to give a residue. Dissolve the residue in dimethylformamide (125 mL). Add dropwise, methyl iodide (19.5 mL, 313 mmol). After 4 hours, dilute the reaction mixture with ethyl acetate and extract with water, saturated aqueous solution of sodium thiosulfate, and brine. Dry over MgSO4, filter through a plug of silica gel eluting with dichloromethane to give the title compound: mp; 101-103° C.

Workup

  1. additionAfter the addition
  2. temperaturewarm the reaction mixture to ambient temperature
  3. customevaporate in vacuo
  4. customto give a residue
  5. additionAdd dropwise
  6. waitAfter 4 hours
  7. extractionextract with water, saturated aqueous solution of sodium thiosulfate, and brine
  8. dry with materialDry over MgSO4
  9. filtrationfilter through a plug of silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-857f9c07510d4c4ea16ed89e0d8e5fae
Source dataset
uspto-grants-1999_07
Patent number
US05922752

Reaction notes

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