Methyl iodide → HCID 67304597, compound

HRID 1009010Notes

Reaction equation

HRID 1009010 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[CH:7][O:6][C:5]=1[CH2:9][OH:10].I[CH3:12]>O1CCCC1>[CH3:12][O:10][CH2:9][C:5]1[O:6][CH:7]=[CH:8][C:4]=1[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11194308(3-methyl-2-furyl)methanol

Product 1

HCID 67304597HCID 67304597, compoundYield 113.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an inert atmosphere sodium hydride (0.25 g ˜60%, 6.2 mmol, 1.1 equiv.) was suspended in dry tetrahydrofuran. At 5° C. a solution of (3-methyl-furan-2-yl)-methanol (0.63 g, 5.6 mmol) in dry tetrahydrofuran was added dropwise. The mixture was stirred at room temp. for one hour, then iodomethane (0.9 g, 6.2 mmol, 1.1 equiv.) was added dropwise. The mixture was stirred overnight at room temp., quenched with diluted acid and extracted with diethyl ether. The combined, organic extracts were washed with brine, dried over magnesium sulfate dihydrate, filtered and concentrated under reduced pressure to give 0.8 g of the title compound as a light yellow oil. GC-MS (EI): M=126.

Workup

  1. stirringThe mixture was stirred overnight at room temp.
  2. customquenched
  3. additionwith diluted acid
  4. extractionextracted with diethyl ether
  5. washorganic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate dihydrate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0962129fe2648a0a9cc6bb8f2222eca
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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