Ethyl (2E)-3-ethoxy-2-butenoate → HCID 178488530, compound

HRID 1796964Notes

Reaction equation

HRID 1796964 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([NH2:15])[CH:11]=[CH:12][C:13]=2[CH3:14])=[C:5]([CH3:16])[CH:4]=1.CCO/[C:20](/[CH3:27])=[CH:21]/[C:22](OCC)=[O:23]>C(Cl)(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]3[N:15]=[C:20]([CH3:27])[CH:21]=[C:22]([OH:23])[C:11]3=[CH:12][C:13]=2[CH3:14])=[C:5]([CH3:16])[CH:4]=1

Participants

5

Reactant 2

HCID 5354173Ethyl (2E)-3-ethoxy-2-butenoateHCID 221747842-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrrol-1-amine

Product 1

HCID 178488530HCID 178488530, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 2-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrrol-1-amine (0.23 g, 1.06 mmol), ethyl trans-3-ethoxycrotonate (0.17 g, 1.06 mmol) and p-toluenesulfonic acid (0.01 g, 0.053 mmol) in CHCl3 (7.0 mL) was refluxed with a Dean-Stark tube charged with molecular sieves for 24 h. After cooling down to room temperature, the mixture was concentrated in vacuo to dryness and the residue was subjected to column chromatography (silica gel, 1/4 EtOAc/heptane) to give 0.194 g (65%) of beige foam as the desired product: mp 234–237° C.; 1H NMR (300 MHz, CDCl3) δ 7.22 (d, J=8 Hz, 1H), 6.89–6.87 (m, 1H), 6.84–6.79 (m, 1H), 6.54 (br s, 1H), 5.94 (br s, 1H), 3.85 (s, 3H), 2.34 (s, 3H), 2.18 (s, 3H), 2.08 (s, 3H); MS m/z 283.2 (M++H).

Workup

  1. temperaturewas refluxed with a Dean-Stark tube
  2. additioncharged with molecular sieves for 24 h
  3. concentrationthe mixture was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-7d3adaae462e41e7bdac2c497441f05e
Source dataset
uspto-grants-2006_04
Patent number
US07034023B2

Reaction notes

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