Potassium Carbonate → HCID 69517548, compound

HRID 854868Notes

Reaction equation

HRID 854868 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:13][C:14]([F:23])([F:22])/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CO>[CH3:12][O:11][C:8]1[C:9]([CH3:10])=[C:2]2[C:3]([CH:4]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]([C:14]([F:13])([F:23])[F:22])[O:1]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoateHCID 105112462-Hydroxy-4-methoxy-3-methylbenzaldehyde

Product 1

HCID 69517548HCID 69517548, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of benzaldehyde from Step 1 (3.0 g, 18.07 mmole) and ethyl 4,4,4-trifluorocrotonate (4.5 g, 27.11 mmole) was dissolved in anhydrous DMF (20 mL), warmed to 60° C. and treated with anhydrous K2CO3 (4.99 g, 36.14 mmole). The solution was maintained at 90° C. for 24 hours. LCMS analysis indicated that the reaction was complete. After the reaction was cooled to room temperature, the solution was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford brown solid, that was dissolved in MeOH (40 mL) and was precipitated upon adding 13 mL water. The suspension was filtered and dried on vacuum yielding a light brown solid: (4.37 g, 76.6%): LCMS m/z339.10 (M+Na). 1H NMR (CDCl3/400 MHz) 7.68 (s, 1H), 7.03(d, 1H, J=8.7 Hz), 6.50 (d, 1H, J=8.7 Hz), 5.70 (q, 1H, J=6 Hz), 4.29 (q, 2H, J=7.2 Hz), 3.84 (s, 3H), 2.09(s, 3H), 1.33 (t, 3H, J=7.2 Hz).

Workup

  1. temperatureThe solution was maintained at 90° C. for 24 hours
  2. temperatureAfter the reaction was cooled to room temperature
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford brown solid, that
  9. customwas precipitated
  10. additionupon adding 13 mL water
  11. filtrationThe suspension was filtered
  12. customdried on vacuum
  13. customyielding a light brown solid

Sources & evidence

ORD record
ord-db8c536894dd4a59ac005e6f1e8f0cf1
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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