Methyl iodide → HCID 15075812, compound

HRID 2073820Notes

Reaction equation

HRID 2073820 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[Li+].CC([N-]C(C)C)C.[F:21][C:22]1[C:27]([Si:28]([CH3:31])([CH3:30])[CH3:29])=[C:26]([F:32])[C:25]([F:33])=[CH:24][C:23]=1[C:34]1[O:35][CH2:36][C:37]([CH3:40])([CH3:39])[N:38]=1.CI>C1COCC1.O>[F:21][C:22]1[C:27]([Si:28]([CH3:31])([CH3:29])[CH3:30])=[C:26]([F:32])[C:25]([F:33])=[C:24]([CH3:1])[C:23]=1[C:34]1[O:35][CH2:36][C:37]([CH3:40])([CH3:39])[N:38]=1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 14774099HCID 14774099, compoundHCID 178418339Butyllithium

Product 1

HCID 15075812HCID 15075812, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.64 ml (4.57 mmol) of diisopropylamine in 20 ml of dry THF under argon was cooled to -78° C. and treated with 2.1 ml (4.20 mmol) of 2.0N n-butyllithium. The LDA solution was stirred at -78° C. for 15 minutes, then warmed to 0° C. To this solution was added a solution of 1.05 g (3.5 mmol) of 2-(2,4,5-trifluoro-3-trimethylsilylphenyl)-4,4-dimethyl-2-oxazoline in 5 ml of THF; the reaction mixture was stirred at 0° C. for 45 minutes, then quenched with 1.50 g (10.6 mmol) of methyl iodide. The solution was stirred at room temperature for three hours and diluted with water. The organic layer was washed with water, dried over magnesium sulfate, and concentrated to give 1.00 g of the title compound as an oil.

Workup

  1. stirringThe solution was stirred at room temperature for three hours
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b0ffcb1cdb264f7281bc9a7ad7c95400
Source dataset
uspto-grants-1990_04
Patent number
US04920120

Reaction notes

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