Methyl iodide → 2-Ethyl-4-methoxybenzoxazole

HRID 275799Notes

Reaction equation

HRID 275799 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[C:6]=2[N:7]=1)[CH3:2].[OH-].[Na+].I[CH3:16]>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:16])[C:6]=2[N:7]=1)[CH3:2]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 156656802-Ethylbenzo[d]oxazol-4-ol

Product 1

HCID 183166412-Ethyl-4-methoxybenzoxazole

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Ethyl-4-hydroxybenzoxazole (4.17 g) was dissolved in tetrahydrofuran (73 ml) at room temperature. Tetrabutylammonium iodide (0.4 g) was added, followed by a solution of sodium hydroxide (3.89 g) in water (40 ml). The mixture was stirred for 10 minutes before addition of iodomethane (3.13 ml). Stirring was then continued overnight. The crude mixture was evaporated onto silica, and purified by flash chromatography eluting with 25% then 50% ethyl acetate in hexane to give the title compound as a straw coloured liquid (3.05 g).

Workup

  1. customThe crude mixture was evaporated onto silica
  2. custompurified by flash chromatography
  3. washeluting with 25%

Sources & evidence

ORD record
ord-7b0d5adfacac440ba9d5a35017e220ec
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Reaction notes

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