Ethyl trifluoroacetate → HCID 17967065, compound

HRID 1767706Notes

Reaction equation

HRID 1767706 reaction equation
[H-].[Na+].[CH3:3][S:4][C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:13])[CH3:12])=[N:9][CH:10]=1.[F:14][C:15]([F:22])([F:21])[C:16](OCC)=[O:17]>O1CCCC1>[F:14][C:15]([F:22])([F:21])[C:16](=[O:17])[CH2:12][C:11]([C:8]1[CH:7]=[CH:6][C:5]([S:4][CH3:3])=[CH:10][N:9]=1)=[O:13]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydrideHCID 200793671-(5-(Methylsulfanyl)pyridin-2-yl)ethan-1-one

Product 1

HCID 17967065HCID 17967065, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirring solution of sodium hydride (0.253 g, 6.31 mmol) in anhydrous tetrahydrofuran (20 mL) was cooled under nitrogen to 0° C. before the addition of 1-(5-methylsulfanyl-pyridin-2-yl)-ethanone (0.880 g, 5.26 mmol) in anhydrous tetrahydrofuran (20 mL). Ethyl trifluoroacetate (0.751 mL, 6.31 mmol) was added dropwise and the reaction allowed to rise in temperature to 22° C., then heated to reflux and stirred under nitrogen for 17 hours. The solvent was removed and the residue partitioned between saturated aqueous ammonium chloride (10 mL) and dichloromethane (10 mL). The aqueous layer was separated and extracted with DCM (×3). The organic layers were combined, dried and the solvent removed to yield the title compound: MS m/z 264 (M+1).

Workup

  1. customto rise in temperature to 22° C.
  2. temperatureheated
  3. temperatureto reflux
  4. customThe solvent was removed
  5. customthe residue partitioned between saturated aqueous ammonium chloride (10 mL) and dichloromethane (10 mL)
  6. customThe aqueous layer was separated
  7. extractionextracted with DCM (×3)
  8. customdried
  9. customthe solvent removed

Sources & evidence

ORD record
ord-4778132dfcb84a13844ce6b9088f24dc
Source dataset
uspto-grants-2007_06
Patent number
US07235560B2

Reaction notes

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