Methyl iodide → HCID 86661510, compound

HRID 2406857Notes

Reaction equation

HRID 2406857 reaction equation
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C@H:7]([CH:12]=[CH2:13])[CH2:8][CH2:9][C:10]#[CH:11])([CH3:4])([CH3:3])[CH3:2].[Li][CH2:17]CCC.CI>C1COCC1>[C:1]([Si:5]([CH3:14])([CH3:15])[O:6][C@H:7]([CH:12]=[CH2:13])[CH2:8][CH2:9][C:10]#[C:11][CH3:17])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 57386253HCID 57386253, compoundHCID 178418339Butyllithium

Product 1

HCID 86661510HCID 86661510, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Compound (4a) (481.6 mg, 2.146 mmol) was dissolved in THF (21.5 mL) and cooled to −78° C. before treated with 1.6 M n-BuLi (2.7 mL, 4.32 mmol) dropwise. The resulting solution was stirred 15 minutes at the same temperature and then methyl iodide (0.67 mL, 1.528 g, 10.765 mmol) was added. During the night the mixture was slowly warmed to room temperature. After 13 hours the reaction was quenched with water. The solution was extracted with ether (3×), the combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. Purification by chromatography (pentane/ether 200/1) provided 395.5 mg of compound (5a) as clear colourless oil with 77% yield.

Workup

  1. temperatureDuring the night the mixture was slowly warmed to room temperature
  2. customAfter 13 hours the reaction was quenched with water
  3. extractionThe solution was extracted with ether (3×)
  4. washthe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography (pentane/ether 200/1)

Sources & evidence

ORD record
ord-6b1f3d19f3eb4625bf3592a40b7ff7bc
Source dataset
uspto-grants-2014_08
Patent number
US08809395B2

Reaction notes

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