Ethyl Acetate → HCID 68160095, compound

HRID 530760Notes

Reaction equation

HRID 530760 reaction equation
C(O[C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1)=[O:5])C.[CH3:15][CH2:16][O:17][C:18]([CH3:20])=[O:19].C(O[K])(C)(C)C>C1(C)C=CC=CC=1>[O:5]=[C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[N:10]=1)[CH2:20][C:18]([O:17][CH2:16][CH3:15])=[O:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 23560697Ethyl 4-(trifluoromethyl)thiazole-2-carboxylateHCID 178418922HCID 178418922, compound

Product 1

HCID 68160095HCID 68160095, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-trifluoromethylthiazole-2-carboxylic acid ethylester (8.88 mmol) in toluene (50 mL) were added successively EtOAc (13.32 mmol) and tBuOK (17.76 mmol). The resulting mixture was stirred at 100° C. for 1 hr. The solvent was removed by evaporation and water and Et2O were added. The solution was neutralized with acetic acid. The extract was washed with water and the organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give compound 28 as a yellow oil in 45% yield. MS (ESI, EI−): m/z=266 (MH−).

Workup

  1. customThe solvent was removed by evaporation and water and Et2O
  2. additionwere added
  3. washThe extract was washed with water
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-145880d0f7ac4c79a88cda401751ec9f
Source dataset
uspto-grants-2016_05
Patent number
US09353100B2

Reaction notes

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