Ethyl trifluoroacetate → HCID 86673605, compound

HRID 1023415Notes

Reaction equation

HRID 1023415 reaction equation
C(O[C:4](=[O:9])[C:5]([F:8])([F:7])[F:6])C.[H-].[Na+].[Cl:12][C:13]1[CH:18]=[C:17]([C:19](=[O:21])[CH3:20])[CH:16]=[CH:15][N:14]=1.[NH4+].[Cl-]>C1COCC1.O.C(O)C>[Cl:12][C:13]1[CH:18]=[C:17]([C:19](=[O:21])[CH2:20][C:4](=[O:9])[C:5]([F:6])([F:7])[F:8])[CH:16]=[CH:15][N:14]=1

Participants

8

Reactant 4

HCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 131452551-(2-Chloropyridin-4-yl)ethan-1-one

Product 1

HCID 86673605HCID 86673605, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Trifluoro-acetic acid ethyl ester (0.30 mL, 2.49 mmol) is added carefully into sodium hydride (60% in mineral oil, 100 mg, 2.49 mmol) suspended in dry THF (2.0 mL) at room temperature. Then 1-(2-chloro-pyridin-4-yl)-ethanone (200 mg, 1.25 mmol) is added into the reaction mixture followed by the addition of ethanol (0.12 mL). The reaction mixture is stirred for 16 hrs and saturated NH4Cl solution (3.0 mL) is added along with 25 mL of water. The mixture is then extracted with EtOAc (3×25 mL). The organic layers are combined and concentrated to give the crude product which is used without purification.

Workup

  1. extractionThe mixture is then extracted with EtOAc (3×25 mL)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d1f2b1136d274e54a9cbda8a9adbaaef
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

Loading…