Methyl iodide → HCID 18969744, compound
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
Product 1
Reagents, catalysts & solvents 1
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
- customquenched with a saturated NH4Cl sol.
- extractionextracted with Et2O
- washThe organic phase was washed with H2O, brine
- dry with materialdried (MgSO4)
- customthe solvents evaporated
- 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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