Methyl iodide → HCID 50853152, compound

HRID 1880440Notes

Reaction equation

HRID 1880440 reaction equation
[OH:1][C:2]1[C:10]2[O:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.C(OCC)(=O)C>[CH3:16][O:1][C:2]1[C:10]2[O:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59560314HCID 59560314, compound

Product 1

HCID 50853152HCID 50853152, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To methyl 7-hydroxy-2-methyl-1,3-benzoxazole-5-carboxylate (400 mg, 2.07 mmol) in DMF (10 mL) was added ground potassium carbonate (570 mg, 4.14 mmol) and methyl iodide (0.142 mL, 2.28 mmol). The reaction was stirred overnight at room temperature. The reaction was diluted with ethyl acetate and washed with water. Organic phase was dried over sodium sulfate, filtered and concentrated to yield 368 mg (73%) of methyl 7-methoxy-2-methyl-1,3-benzoxazole-5-carboxylate as an off white solid. LC/MS=222 (M+H).

Workup

  1. washwashed with water
  2. dry with materialOrganic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9949428f683342ef91e7aa40c07e9db0
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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