Pyridine → Ethyl 3-(4-methylphenyl)-2-propenoate

HRID 493159Notes

Reaction equation

HRID 493159 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([O-])=O.N1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.N1C=CC=[CH:18][CH:17]=1>>[CH2:8]([O:7][C:1](=[O:6])[CH:2]=[CH:3][C:11]1[CH:18]=[CH:17][C:14]([CH3:15])=[CH:13][CH:12]=1)[CH3:9]

Participants

4

Reactant 3

HCID 1049PyridineHCID 8082PiperidineHCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 334099Ethyl 3-(4-methylphenyl)-2-propenoateYield 792%

Procedure

A solution of 3 (11.6 g, 96.9 mmol) and 4 (16.7 g, 126 mmol) in piperidine (958 μL, 9.69 mmol) and pyridine (39.2 mL, 485 mmol) was refluxed for 8 h under argon. The reaction mixture was cooled to room temperature and the reaction was quenched with 2 N HCl (˜250 mL). The reaction mixture was extracted with ether. The extracts were washed with water, base (NaHCO3), and water. The organic solution was dried (Na2SO4), concentrated, and chromatographed (silica, CH2Cl2) to give a colorless oil (14.6 g, 79%): 1H NMR δ 1.33 (t, J=7.2 Hz, 3H), 2.37 (s, 3H), 4.26 (q, J=7.2 Hz, 2H), 6.39 (d, J=15.8 Hz, 1H), 7.18 (d, J=8.2 Hz, 2H), 7.42 (d, J=8.2 Hz, 2H), 7.66 (d, J=15.8 Hz, 1H); 13C NMR δ 14.5 21.6, 60.6, 117.4, 128.2, 129.8, 131.9, 140.8, 144.8, 167.4; Anal. Calcd for C12H14O2: C, 75.76; H, 7.42. Found: C, 75.76; H, 7.44.

Workup

  1. customthe reaction was quenched with 2 N HCl (˜250 mL)
  2. extractionThe reaction mixture was extracted with ether
  3. washThe extracts were washed with water, base (NaHCO3), and water
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. concentrationconcentrated
  6. customchromatographed (silica, CH2Cl2)

Sources & evidence

ORD record
ord-56a66f4a64d44813b17870910857207b
Source dataset
uspto-grants-2009_05
Patent number
US07534807B2

Reaction notes

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