Methyl iodide → Methyl 2-oxotetrahydrofuran-3-carboxylate

HRID 2116463Notes

Reaction equation

HRID 2116463 reaction equation
[C:1]1([C:7]([OH:9])=[O:8])([C:4]([OH:6])=[O:5])[CH2:3][CH2:2]1.[CH2:10](N(CC)CC)C.IC>C(#N)C>[O:6]=[C:4]1[CH:1]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2][O:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 690171,1-Cyclopropanedicarboxylic acid

Product 1

HCID 315161Methyl 2-oxotetrahydrofuran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

Cyclopropane-1,1-dicarboxylic acid (10 g) in acetonitrile(200 ml) was treated with triethylamine (43 ml) and iodomethane (19 ml) at room temperature. The solution was stirred for 2 h then heated at 75° C. for 16 h. The solvent was removed under reduced pressure, the residue dissolved in water, extracted with ethyl acetate, dried(MgSO4) and evaporated to a brown oil (6.70 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with ethyl acetate, dried(MgSO4)
  4. customevaporated to a brown oil (6.70 g)

Sources & evidence

ORD record
ord-271cb19a613e45acb5bdc3c977df1744
Source dataset
uspto-grants-2008_10
Patent number
US07439240B2

Reaction notes

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