Tetrahydrofuran → ethyl (E)-3-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]propenoate

HRID 1604634Notes

Reaction equation

HRID 1604634 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[O:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.CC(C)([O-:29])C.[K+]>CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16](/[CH:19]=[CH:23]/[C:22]([O:21][CH2:25][CH3:24])=[O:29])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 196038064-Tert-butyl-2-(5-formylbenzofuran-2-yl)thiazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 86754881ethyl (E)-3-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]propenoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole (1.83 g) and triethyl phosphonoacetate (1.53 ml) in the mixed solvent of tetrahydrofuran (10 ml) and N,N-dimethylformamide (10 ml) was stirred under ice-cooling. After several minutes, potassium tert-butoxide was added to the mixture, which was stirred for 1 hour at same temperature. The resulting mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give ethyl (E)-3-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]propenoate (0.68 g).

Workup

  1. temperaturecooling
  2. waitAfter several minutes
  3. stirringwas stirred for 1 hour at same temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a syrup
  9. washeluted with a mixture of n-hexane and ethyl acetate
  10. additionThe fractions containing the objective compound
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b71855787de84e5faf787b7674828d61
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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