Toluene → HCID 59363834, compound

HRID 1430626Notes

Reaction equation

HRID 1430626 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].C(CC(=O)C)(=O)C.[C:24]1(C)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:1]([O:3][C:4](=[O:16])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[C:26]([CH3:27])=[CH:25][CH:24]=[C:29]2[CH3:28])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

4

Reactant 3

HCID 1140TolueneHCID 31261AcetylacetoneHCID 22060556HCID 22060556, compound

Product 1

HCID 59363834HCID 59363834, compoundYield 71%

Procedure

2-(3-Amino-phenoxy)-2-methyl-propionic acid ethyl ester (0.52 g, 2.36 mmol) was dissolved in Toluene (2 ml) and acetylacetone (0.53 m, 4.4 mmol) was added to the solution. The resulting mixture was refluxed for 6 h with a Dean-Stack apparatus. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The crude material thus obtained was purified by flash column affording 2-[3-(2,5-Dimethyl-pyrrol-1-yl)-phenoxy]-2-methyl-propionic acid ethyl ester (0.5 g, 71%). 1H NMR (400 MHz, CDCl3): 1.): 1.24 (t, J=7.2 Hz, 3H), 1.57 (s, 6H), 2.02 (s, 6H), 4.23 (q, J=7.2 Hz, 2H), 5.88 (s, 2H), 6.71 (s, 1H), 6.83-6.91 (m, 2H), 7.26-7.33 (m, 1H); MS (EI) m/z: 302 (M+1).

Workup

  1. temperatureThe resulting mixture was refluxed for 6 h with a Dean-Stack apparatus
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material thus obtained
  4. customwas purified by flash column

Sources & evidence

ORD record
ord-418acf4ebf924feda24b9e0ca2ce01fb
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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