2-Acetylthiophene → Ethyl 3-oxo-3-(thiophen-2-yl)propanoate

HRID 424390

Reaction equation

HRID 424390 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:8])[CH3:7].[H-].[Na+].[C:11](=O)([O:15]CC)[O:12][CH2:13][CH3:14]>>[O:8]=[C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:7][C:11]([O:12][CH2:13][CH3:14])=[O:15]

Participants

4

Reactant 3

HCID 69202-AcetylthiopheneHCID 7766Diethyl CarbonateHCID 24758Sodium hydride

Product 1

HCID 255159Ethyl 3-oxo-3-(thiophen-2-yl)propanoate

Conditions

Temperature
71 °C

Procedure

To a solution of 1-(thiophen-2-yl)ethanone (2.944 g, 23.3 mmol) and Diethyl carbonate (70 mL) at 0° C. was added sodium hydride (1.86 g, 46.6 mmol). The resulting off-white slurry solution was gradually warmed to 71° C., and stirred for 1.5 hour. The reaction mixture was poured into ice-HOAc—H2O, and extracted with ethyl acetate. The organic phase was washed (brine), dried (MgSO4) and concentrated to give a brown liquid. The crude product was purified via flash chromatography (silica gel cartridge with eluent of 0-3% ethyl acetate/hexane) to afford ethyl 3-oxo-3-(thiophen-2-yl)propanoate as an amble liquid, 4.193 g (91%). LCMS m/z 388.99, 390.09 (M+23); HPLC: Rt 2.01 min. (4.0 min. gradient, Column: YMC Combiscreen C-18, Method A).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed (brine)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a brown liquid
  6. customThe crude product was purified via flash chromatography (silica gel cartridge with eluent of 0-3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4227d811ef7a42908acad62aba526e0a
Source dataset
uspto-grants-2012_01
Patent number
US08106046B2

Linked notes

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