Methylparaben → HCID 67354853, compound

HRID 1946637Notes

Reaction equation

HRID 1946637 reaction equation
Br[CH2:2][C:3]([N:5]1[CH:11]=[C:10]2[CH2:12][CH:13]=[CH:14][CH:15]=[C:9]2[O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)=[O:4].[OH:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[CH2:12]1[C:10]2=[CH:11][N:5]([C:3](=[O:4])[CH2:2][O:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=3)[C:6]3[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=3[O:8][C:9]2=[CH:15][CH:14]=[CH:13]1

Participants

6

Reactant 3

HCID 7456MethylparabenHCID 10796Cesium carbonateHCID 67355253HCID 67355253, compound

Product 1

HCID 67354853HCID 67354853, compoundYield 32.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Title compound 455 (0.890 g, 2.81 mmol) and the methyl 4-hydroxybenzoate (0.512 g, 3.37 mmol) were dissolved in acetonitile (10.0 mL) and the cesium carbonate (1.83 g, 5.62 mmol) was added. The reaction mixture was stirred at 100° C. in a sealed tube for 4 hours. The mixture was cooled down to room temperature and diluted with ethyl acetate. The organic layer was washed with water (2 times) and brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography (30-40% ethyl acetate in hexanes) to afford title compound 456 (355 mg, 32%) as white foam. MS (m/z): 390.3 (M+H).

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. washThe organic layer was washed with water (2 times) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude was purified by flash chromatography (30-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-838516b89dbd492980ee5a884b51371f
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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