Potassium Carbonate → Diethyl 2,6-diisopropyl-4-(2-ethynylphenyl)pyridine-3,5-dicarboxylate

HRID 324862Notes

Reaction equation

HRID 324862 reaction equation
[CH:1]([C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]#[C:22][Si](C)(C)C)[C:7]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:6]([CH:32]([CH3:34])[CH3:33])[N:5]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C>[CH:32]([C:6]1[C:7]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]#[CH:22])[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH:1]([CH3:2])[CH3:3])[N:5]=1)([CH3:34])[CH3:33]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 22005127Diethyl 2,6-diisopropyl-4-[(2-trimethylsilylethynyl)phenyl]pyridine-3,5-dicarboxylate

Product 1

HCID 22005317Diethyl 2,6-diisopropyl-4-(2-ethynylphenyl)pyridine-3,5-dicarboxylateYield 80.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.68 g (11.9 mmole) of the intermediate obtained in Step B in 800 mL ethanol was treated with 2.8 g (20.3 mmole) of potassium carbonate and the reaction mixture was allowed to stir at room temperature for 16 hours. The mixture was diluted with ethyl acetate and washed with saturated aqueous solution of ammonium chloride, brine and separated. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by flash silica gel chromatography, eluting with 10 ethyl acetate/n-hexane, to give 3.95 g (9.6 mmole) of the product. 1H NMR (300 MHz, CDCl3): δ 0.90 (t, J=7.0 Hz, 6 H), 1.32 (m, 12 H), 2.97 (s, 1 H), 3.21 (septet, J=6.6, 2 H), 3.90 (q, J=7.0, 4 H), 7.2-7.6 (m, 4 H).

Workup

  1. washwashed with saturated aqueous solution of ammonium chloride, brine
  2. customseparated
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by flash silica gel chromatography
  7. washeluting with 10 ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-99a7df30163c40c89990deed7feea639
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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