2,2,2-Trifluoroethanol → Methyl 5-(2,2,2-trifluoroethoxy)pyrazine-2-carboxylate

HRID 627725Notes

Reaction equation

HRID 627725 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[F:12][C:13]([F:17])([F:16])[CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>>[F:12][C:13]([F:17])([F:16])[CH2:14][O:15][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 11430Potassium CarbonateHCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 57827340Methyl 5-(2,2,2-trifluoroethoxy)pyrazine-2-carboxylateYield 80.5%

Procedure

To a mixture of methyl 5-chloropyrazine-2-carboxylate (1 g, 5.79 mmol) and 2,2,2-trifluoroethanol (2.111 ml, 29.0 mmol) was added potassium carbonate (0.801 g, 5.79 mmol). The reaction was stirred at ambient temperature for 16 hrs. The reaction was partitioned between ethyl acetate and water. The organic portion was concentrated and purified in 10-60% EtOAc/Heptane to give the title compound (1.1 g, 4.66 mmol, 80%). MS m/z=237.1 (M+H).

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. concentrationThe organic portion was concentrated
  3. custompurified in 10-60% EtOAc/Heptane

Sources & evidence

ORD record
ord-dc05ada07aec4889bdc97e1d10afe713
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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