Potassium Carbonate → HCID 68617143, compound

HRID 1158471Notes

Reaction equation

HRID 1158471 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([OH:13])[CH:6]=1)[CH3:2].[F:15][C:16]([F:25])([F:24])[CH2:17][CH2:18]OS(C)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH2:18][CH2:17][C:16]([F:25])([F:24])[F:15])[CH:6]=1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15480330Ethyl 3-hydroxy-4-methoxybenzoateHCID 252105013,3,3-Trifluoropropyl methanesulfonate

Product 1

HCID 68617143HCID 68617143, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 3-hydroxy-4-methoxy-benzoic acid ethyl ester (1.75 g, 8.92 mmol), methanesulfonic acid 3,3,3-trifluoro-propyl ester (2.06 g, 10.7 mmol) and anhydrous K2CO3 (2.49 g, 17.8 mmol) in acetone (20 mL) is heated with stirring at reflux temperature overnight. After cooling, the mixture is diluted with AcOEt followed by washing of the organic phase with 2N aqueous NaOH and brine. The organic layer is dried over Na2SO4 and evaporated, and the crude product is purified by silica gel chromatography (eluent: hexane/AcOEt 5:1) to give the title compound as oil. TLC, Rf (hexane/AcOEt 1:1)=0.59. MS: 293.0 [M+H]+. 1H-NMR (CDCl3): δ 1.42 (t, 3H), 2.74 (m, 2H), 3.96 (s, 3H), 4.33 (m, 2H), 4.40 (m, 2H), 6.94 (m, 1H), 7.59 (s, 1H), 7.77 (m, 1H) ppm.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature overnight
  3. temperatureAfter cooling
  4. washby washing of the organic phase with 2N aqueous NaOH and brine
  5. dry with materialThe organic layer is dried over Na2SO4
  6. customevaporated
  7. customthe crude product is purified by silica gel chromatography (eluent: hexane/AcOEt 5:1)

Sources & evidence

ORD record
ord-6f91a604098f4eedaf6c16790a1d13f8
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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