Potassium Carbonate → HCID 57899230, compound

HRID 1802771Notes

Reaction equation

HRID 1802771 reaction equation
[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][NH:13]2)=[CH:8][CH:7]=1.[C:18]1(C)[CH:23]=CC(S(OCCC#C)(=O)=O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:20][CH2:19][C:18]#[CH:23])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2720203-Butynyl p-toluenesulfonateHCID 57899223HCID 57899223, compound

Product 1

HCID 57899230HCID 57899230, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of (E)-3-(4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester (5.52 g, 20.6 mmol), 3-butynyl p-toluenesulfonate (4.55 mL, 24.7 mmol) and potassium carbonate (5.98 g, 43.3 mmol) in acetonitrile (15 mL) was heated at 65° C. for 9 h. After cooled to room temperature, the reaction mixture was filtered, concentrated, and purified via silica gel column chromatography, and the residue was recrystallized from heptane to provide (E)-3-[4-(1-but-3-ynyl-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester (3.68 g, 63% yield). LCMS (m/z): 284.2 (M+1).

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. custompurified via silica gel column chromatography
  5. customthe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-9ffdf8843ff744c0a24361bffb5c1610
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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