Ethyl Propionate → 1-(Thiazol-2-yl)propanone

HRID 260418Notes

Reaction equation

HRID 260418 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li][CH2:7][CH2:8][CH2:9]C.C(OCC)(=[O:14])CC>C1COCC1>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:7][C:8](=[O:14])[CH3:9]

Participants

5

Reactant 3

HCID 7749Ethyl PropionateHCID 9256ThiazoleHCID 178418339Butyllithium

Product 1

HCID 231799141-(Thiazol-2-yl)propanoneYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of thiazole (10 g, 0.12 mol) in dry THF (100 mL) at -78° C. was added BuLi (50 mL, 2.47M in hexane). The resulting reaction mixture was stirred 30 min. then ethyl propionate (18.8 mL, 0.16 mol) in THF was added and the cooling bath was removed. After 30 min. an aqueous solution of NH4OAc (25%) was added and the THF evaporated. Ether was added and washed successively with H2O, brine, dried over MgSO4 and evaporated. The residue was distilled under vacuum to give 12.1 g (73%) of the title compound.

Workup

  1. customThe resulting reaction mixture
  2. customthe cooling bath was removed
  3. additionAfter 30 min. an aqueous solution of NH4OAc (25%) was added
  4. customthe THF evaporated
  5. additionEther was added
  6. washwashed successively with H2O, brine
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-303de2b4e5b74c199fda5bfbbc6f0fa2
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Reaction notes

Loading…