Ethyl benzoate → 1-Phenyl-2-(thiazol-2-yl)ethanone

HRID 924925Notes

Reaction equation

HRID 924925 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Li]CCCC.[C:12](OCC)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCOC(C)=O>C1COCC1>[C:13]1([C:12](=[O:19])[CH2:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7165Ethyl benzoateHCID 8857Ethyl AcetateHCID 771292-MethylthiazoleHCID 178418339Butyllithium

Product 1

HCID 178870471-Phenyl-2-(thiazol-2-yl)ethanoneYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-methylthiazole (500 mg, 5.1 mmol) in anhydrous THF (10 mL) at −78° C. under nitrogen was added dropwise n-BuLi (2.5 mol/L, 2.0 mL), after being stirred at this temperature for 1 hour, a solution of ethyl benzoate (1.1 g, 7.3 mmol) in anhydrous THF (5 mL) was added, and the reaction mixture was stirred at room temperature overnight. When TLC (PE:EtOAc=7:1) indicated that the starting materials were consumed, water was added to quench the reaction, and the aqueous layer extracted with EtOAc (10 mL×3). The combined organic layer was washed with brine (10 mL), dried over Na2SO4, filtered, concentrated, and purified by column chromatography (PE:EtOAc=15:1) to afford Intermediate 3 as a yellow oil (170 mg, yield: 17.0%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customwere consumed
  3. additionwater was added
  4. customto quench
  5. customthe reaction
  6. extractionthe aqueous layer extracted with EtOAc (10 mL×3)
  7. washThe combined organic layer was washed with brine (10 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by column chromatography (PE:EtOAc=15:1)

Sources & evidence

ORD record
ord-55ed2a6bd27244b4bcd1bddda71e2f09
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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