Potassium Carbonate → HCID 54468434, compound

HRID 2106667Notes

Reaction equation

HRID 2106667 reaction equation
Br[CH2:2][CH2:3][CH:4]=[C:5]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH:23]1[CH2:33][CH2:32][CH2:31][CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24]1>CC(C)=O>[CH2:29]([O:28][C:26](=[O:27])[CH:25]1[CH2:31][CH2:32][CH2:33][N:23]([CH2:2][CH2:3][CH:4]=[C:5]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:24]1)[CH3:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98969Ethyl nipecotateHCID 54418432HCID 54418432, compound

Product 1

HCID 54468434HCID 54468434, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromo-4-(2-furanyl)-4-phenylbut-3-ene (0.23 g, 0.83 mmol) was dissolved in anhydrous acetone (10 ml) and dried potassium carbonate (0.46 g, 3.32 mmol) was added, followed by ethyl nipecotate (0.16 g, 1 mmol). The suspension was stirred at room temperature for 9 days, filtered and evaporated to a residue. The residue was purified by column chromatography on silica gel (Merck Art 9385), eluting with heptane/tetrahydrofuran (7:3), to provide the title ester (140 mg, 47%) as an oil. T.l.c. rf=0.36 (SiO2, heptane/THF (7:3)).

Workup

  1. filtrationfiltered
  2. customevaporated to a residue
  3. customThe residue was purified by column chromatography on silica gel (Merck Art 9385)
  4. washeluting with heptane/tetrahydrofuran (7:3)

Sources & evidence

ORD record
ord-f41f33c150074e6fb7f6e5a26790bee0
Source dataset
uspto-grants-1990_06
Patent number
US04931450

Reaction notes

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