Methyl iodide → HCID 14326177, compound

HRID 1606880Notes

Reaction equation

HRID 1606880 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8])=[CH:2]1.[CH3:12]C(C)([O-])C.[K+].IC>C1COCC1.CCOCC.C1OCCOCCOCCOCCOCCOC1>[CH3:12][N:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8])=[CH:2]1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 19785053HCID 19785053, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14326177HCID 14326177, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl pyrrol-3-yloxoacetate (3.3 g, 22 mol) in THF (70 ml) was added at room temperature to a stirred suspension of potassium tert-butoxide (2.7 g, 24 mmol) and 18-crown-6 (0.1 g, 0.39 mmol) in ether (250 ml). The reaction mixture was stirred for 30 minutes then iodomethane (1.6 ml, 26 mmol) in ether (50 ml) was added dropwise. The reaction mixture was stirred for 16 hours then filtered through hyflo supercell and washed with brine, dried and concentrated to give methyl N-methyl-pyrrol-3-yloxoacetate (2.84 g, 79% yield) as a clear oil, IR (thin film) 1725, 1645 cm-1, 1H nmr: delta 3.64 (3H, s), 3.85 (3H, s), 6.5 (1H, m) 6.7 (1H, m), 7.6 (1H, m) ppm.

Workup

  1. stirringThe reaction mixture was stirred for 16 hours
  2. filtrationthen filtered through hyflo supercell
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fa62c82e258a49019844f3808fbef996
Source dataset
uspto-grants-1989_09
Patent number
US04863503

Reaction notes

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