Methane → HCID 54238021, compound

HRID 1290213Notes

Reaction equation

HRID 1290213 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.CO[CH:17]1[CH2:21][CH2:20][CH:19](OC)O1.C>C1(C)C=CC=CC=1.C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=2)[CH:17]=[CH:21][CH:20]=[CH:19]1

Participants

6

Reactant 3

HCID 297MethaneHCID 790982,5-DimethoxytetrahydrofuranHCID 97826Ethyl 3-(4-aminophenyl)acrylate

Product 1

HCID 54238021HCID 54238021, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

A solution of ethyl 4-aminocinnamate (1 g) and 2,5-dimethoxytetrahydrofuran (0.677 ml) in toluene (3 ml) and acetic acid (3 ml) was refluxed for 5 hours with removing methane. After cooling, the mixture was washed with water twice and saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. The residue was purified with column chromatography eluting with n-hexane-ethyl acetate to give ethyl 4-(1-pyrrolyl)cinnamate (740 mg) as colorless crystals.

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed with water twice
  3. dry with materialsaturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customThe residue was purified with column chromatography
  6. washeluting with n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-990a0e1a0ec64458af6770cc3dda29a0
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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