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

HRID 324862

반응식

HRID 324862 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-99a7df30163c40c89990deed7feea639
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218431B1

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