Ethyl Glycolate → Ethyl 2-pyrimidinyloxyacetate

HRID 1070517

Reaction equation

HRID 1070517 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][OH:3].[H-].[Na+].Cl[C:11]1[N:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[Cl-].[NH4+]>O1CCCC1>[N:12]1[CH:13]=[CH:14][CH:15]=[N:16][C:11]=1[O:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 744042-Chloropyrimidine

Product 1

HCID 22396258Ethyl 2-pyrimidinyloxyacetateYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl glycolate (1.04 g) was dissolved in tetrahydrofuran (10 ml) and the solution was cooled to 0° C. Sodium hydride (60% suspension in oil, 0.43 g) was added and the suspension was stirred and then sonicated in an ultrasonic bath. 2-Chloropyrimidine (1.14 g) was added and the mixture was sonicated for a further 110 min. Ammonium chloride solution was added and the mixture was extracted thrice with ethyl acetate, the organic phases were washed with brine and dried, filtered and evaporated. The residue was purified by chromatography eluting with iso-hexane:ethyl acetate (13:7) to give the subtitle compound (1.40 g) as an oil.

Workup

  1. customsonicated in an ultrasonic bath
  2. customthe mixture was sonicated for a further 110 min
  3. extractionthe mixture was extracted thrice with ethyl acetate
  4. washthe organic phases were washed with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography
  9. washeluting with iso-hexane:ethyl acetate (13:7)

Sources & evidence

ORD record
ord-7a6f9565a97145d29f1adc35a6d34fb6
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Linked notes

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