Ethyl Acetate → 3-(1,3-Thiazol-4-yl)propanal

HRID 1096811Notes

Reaction equation

HRID 1096811 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH:8]([OH:11])CO)[N:3]=[CH:2]1.CCOC(C)=O>C1COCC1.O>[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH:8]=[O:11])[N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 66783589HCID 66783589, compound

Product 1

HCID 451216853-(1,3-Thiazol-4-yl)propanalYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaIO4 (2.40 g, 11.3 mmol) was added to a sol. of (rac.)-4-thiazol-4-ylbutane-1,2-diol (1.62 g, 9.37 mmol) in THF (20 mL) and water (10 mL). The mixture was stirred for 2 h, and EtOAc was added. The mixture was washed with brine, and with aq. sat. NaHCO3. The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (1.04 g, 79%), which was used further without purification. LC-MS: tR=0.32, ES+: 142.11.

Workup

  1. washThe mixture was washed with brine
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-fee6b191efba4b32be4b55d1fff422eb
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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