Methyl iodide → HCID 15075812, compound

HRID 1081397Notes

Reaction equation

HRID 1081397 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 3 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 3 hours
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f3cfe5a9a3194d169a4ed897249b671a
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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