Sodium hydride → 3-(2,2,2-Trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester

HRID 517071Notes

Reaction equation

HRID 517071 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4].[H-].[Na+].FC(F)(F)S(O[CH2:20][C:21]([F:24])([F:23])[F:22])(=O)=O>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:10]([O:11][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylate

Product 1

HCID 574758803-(2,2,2-Trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-hydroxy-pyridine-2-carboxylic acid methyl ester (200 mg, 1.3 mmol) in N,N-dimethylformamide (2.0 ml) was added at 22° C. sodium hydride (55% in oil, 64 mg) and stirring was continued until gas evolution ceased. The suspension was cooled to 0° C. and treated with trifluoroethyl trifluoromethanesulfonate (728 mg) and stirring was continued at 22° C. for 2 hours. The mixture was partitioned between saturated sodium hydrogen-carbonate solution and ethyl acetate, and the organic layer was dried and evaporated. The residue was purified by chromatography on silica using n-heptane and ethyl acetate (3:1) as the eluent to give 3-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester as a pale green oil. MS (ISP): m/z=236 [M+H]+.

Workup

  1. stirringstirring
  2. customThe mixture was partitioned between saturated sodium hydrogen-carbonate solution and ethyl acetate
  3. customthe organic layer was dried
  4. customevaporated
  5. customThe residue was purified by chromatography on silica

Sources & evidence

ORD record
ord-8303201e43a443e98e6d5f6fd67e0536
Source dataset
uspto-grants-2015_08
Patent number
US09115098B2

Reaction notes

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