Methyl iodide → HCID 18969744, compound

HRID 399067Notes

Reaction equation

HRID 399067 reaction equation
[CH3:1][N:2]([CH3:11])[C:3](=[O:10])[CH2:4][C:5]1[CH:9]=[CH:8][S:7][CH:6]=1.[Li+].[CH3:13]C([N-]C(C)C)C.CI>C1COCC1>[CH3:11][N:2]([CH3:1])[C:3](=[O:10])[CH:4]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)[CH3:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 23273495Thiophene,3-(N,N-diMe acetamido)

Product 1

HCID 18969744HCID 18969744, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of acetamide from Step 1 (510 mg) in THF (15 mL) at -78° C. was added LDA (mono THF, 1.5M, cyclohexane, 250 μL) followed by MeI (700 μL) after 30 min. The mixture was warmed to r.t., quenched with a saturated NH4Cl sol. and then extracted with Et2O. The organic phase was washed with H2O, brine, dried (MgSO4) and the solvents evaporated. The residue was purified by flash chromatography (silica gel; hexane/EtOAc (60:40)) to afford the title compound as a oil.

Workup

  1. customquenched with a saturated NH4Cl sol.
  2. extractionextracted with Et2O
  3. washThe organic phase was washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. customthe solvents evaporated
  6. customThe residue was purified by flash chromatography (silica gel; hexane/EtOAc (60:40))

Sources & evidence

ORD record
ord-94db0e5ad56541c6b9bafec4d3fad021
Source dataset
uspto-grants-1998_10
Patent number
US05817700

Reaction notes

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