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

HRID 324862ノート

反応式

HRID 324862 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-99a7df30163c40c89990deed7feea639
出典データセット
uspto-grants-2001_04
特許番号
US06218431B1

反応ノート

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