Methyl iodide → HCID 66841656, compound

HRID 1929001Notes

Reaction equation

HRID 1929001 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[CH2:13]([N:20]1[CH2:25][CH2:24]/[C:23](=[N:26]\[N:27]([CH3:29])[CH3:28])/[CH:22]([CH3:30])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CI>C1COCC1.ClCCl>[CH2:13]([N:20]1[CH2:25][CH:24]([CH3:1])[C:23](=[N:26][N:27]([CH3:29])[CH3:28])[CH:22]([CH3:30])[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 18606553HCID 18606553, compoundHCID 178418339Butyllithium

Product 1

HCID 66841656HCID 66841656, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-5 °C

Procedure

Diisopropylamine (3.3 ml, 23.5 mmol) is dissolved in 20 ml of THF and cooled to −5° C. A 1.6M solution of n-butyllithium in THF (14.7 ml, 23.5 mmol) is added dropwise within 10 min. After additional 10 min at −5° C., a solution of 42 (4.8 g, 19.6 mmol) in 30 ml of THF is added within 20 min (the color of the reaction mixture changed to red). Now, the solution is cooled to −78 C. Methyliodide (1.33 ml, 21.5 mmol) is added dropwise within 15 min and the mixture is allowed to warm to room temperature over night. Dichloromethane is added and the solution is washed with water. Evaporation gave 5 g of a colorless oil, which is further purified by flash-chromatography (silicagel, ethyl acetate/hexanes 1:1)

Workup

  1. temperatureNow, the solution is cooled to −78 C
  2. temperatureto warm to room temperature over night
  3. washthe solution is washed with water
  4. customEvaporation

Sources & evidence

ORD record
ord-afc86fa6e31444c0baa3d2d4bcaee723
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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