Ethyl orthoformate → Methyl 2-(benzo[d]oxazol-5-yl)acetate

HRID 660277Notes

Reaction equation

HRID 660277 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([NH2:12])[CH:6]=1.[CH:14](OCC)(OCC)OCC>O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]2[O:11][CH:14]=[N:12][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 1475136Methyl 2-(3-amino-4-hydroxyphenyl)acetate

Product 1

HCID 16413026Methyl 2-(benzo[d]oxazol-5-yl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl-2-(3-amino-4-hydroxyphenyl)acetate (1.39 g, 7.67 mmol) was combined at RT with triethyl orthoformate (10 ml). The reaction mixture was heated to reflux for 12 h and then cooled to RT. Water (70 mL) was added thereto and the reaction mixture was extracted with EA. The combined organic phases were dried over MgSO4 and filtered. The solvent was removed under a vacuum and the residue purified by means of column chromatography (n-hexane/EA=2:1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 h
  3. extractionthe reaction mixture was extracted with EA
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under a vacuum
  7. customthe residue purified by means of column chromatography (n-hexane/EA=2:1)

Sources & evidence

ORD record
ord-6d899332cb7140c3ac23056d1c6960da
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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