Methanol → HCID 54238021, compound

HRID 1900028Notes

Reaction equation

HRID 1900028 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.CO>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 887MethanolHCID 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 methanol. 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-1db1a249ff6741ee8cf2ffcbc8e0be70
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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