Methyl iodide → HCID 67243804, compound

HRID 2425719Notes

Reaction equation

HRID 2425719 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])[CH:7]=[CH:6][C:5]=1[I:15])[CH3:2].[H-].[Na+].I[CH3:19]>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:14])([CH3:13])[CH2:11][O:12][CH3:19])[CH:7]=[CH:6][C:5]=1[I:15])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67244628HCID 67244628, compound

Product 1

HCID 67243804HCID 67243804, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-ethoxy-4-(2-hydroxy-1,1-dimethylethyl)iodobenzene (1.0 g, 3.123 mmol, example 4) in tetrahydrofuran cooled to 0° C. was added sodium hydride (150 mg, 6.246 mmol, 60% in mineral oil). Iodomethane (0.58 mL, 9.369 mmol) was added after 15 min. The icebath was then removed and the reaction mixture was stirred at room temperature for 12 h. Saturated solution of ammonium chloride was added and the mixture was partitioned between ethyl acetate (20 mL) and water (5 mL). The product was extracted with ethyl acetate (2×). The organic layers were washed with water (1×), brine (1×), dried over anhydrous sodium sulfate and concentrated. Purification of the crude residue by flash column chromatography (silica gel, eluting with a gradient of 0-60% ethyl acetate in hexanes) gave 2-ethoxy-4-(2-methoxy-1,1-dimethylethyl)iodobenzene (891 mg, 85% yield) as clear oil.

Workup

  1. customThe icebath was then removed
  2. additionSaturated solution of ammonium chloride was added
  3. customthe mixture was partitioned between ethyl acetate (20 mL) and water (5 mL)
  4. extractionThe product was extracted with ethyl acetate (2×)
  5. washThe organic layers were washed with water (1×), brine (1×)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customPurification of the crude residue by flash column chromatography (silica gel
  9. washeluting with a gradient of 0-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-eb8041eae3174e77b5fd46cb2772bd9e
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

Loading…