Ethyl Glycolate → Ethyl [(6-Methyl-1,3-benzoxazol-2-yl)oxy]acetate

HRID 1666702Notes

Reaction equation

HRID 1666702 reaction equation
[OH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl[C:11]1[O:12][C:13]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:14]=2[N:15]=1>O1CCCC1>[CH3:20][C:18]1[CH:17]=[CH:16][C:14]2[N:15]=[C:11]([O:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[O:12][C:13]=2[CH:19]=1

Participants

5

Reactant 3

HCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 106786662-Chloro-6-methyl-benzooxazole

Product 1

HCID 86761430Ethyl [(6-Methyl-1,3-benzoxazol-2-yl)oxy]acetateYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.73 g (7 mmol) ethyl hydroxyacetate is dissolved in 20 ml tetrahydrofurane and 0.36 g (9 mmol) 60% sodium hydride is added to it. After 20 minute stirring 1.0 g (6 mmol) 2-chloro-6-methyl-1,3-benzoxazole is added and the mixture is heated under reflux for 3 hours. The solvent is removed, the residue is dissolved in 15 ml water, extracted with 3×20 ml ethyl acetate. The united organic phase is dried over sodium sulfate and evaporated to obtain 1.3 g title compound as an oil. LC-MS[MH+]=236 (C12H13NO4 235.24)

Workup

  1. additionis added
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 3 hours
  4. customThe solvent is removed
  5. dissolutionthe residue is dissolved in 15 ml water
  6. extractionextracted with 3×20 ml ethyl acetate
  7. dry with materialThe united organic phase is dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-615824c0007b4ceeb87e2c9b8bce3f14
Source dataset
uspto-grants-2011_10
Patent number
US08044078B2

Reaction notes

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