Cesium carbonate → 3-Ethynyl-5-(1-methyl-2-pyrrolidinyl)pyridine

HRID 233749ノート

反応式

HRID 233749 の反応式
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH3:18])[CH:10]=[N:11][CH:12]=1)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CO>[C:6]([C:7]1[CH:8]=[C:9]([CH:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH3:18])[CH:10]=[N:11][CH:12]=1)#[CH:5]

参加物

4

反応物 2

HCID 10796Cesium carbonateHCID 196942995-Trimethylsilylethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine

生成物 1

HCID 1331063-Ethynyl-5-(1-methyl-2-pyrrolidinyl)pyridine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Repeating the procedure of Example 16, but using trimethylsilylacetylene in place of phenylacetylene, 5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine and the fumarate derivative thereof were obtained as follows. 5-Trimethylsilylethynyl-3-(1-methyl-2-pyrrolidinyl) pyridine (516 mg, 2 mmol) and cesium carbonate (200 mg, 0.6 mmol) were dissolved in methanol (10 mL) and heated under reflux for 5 h. After cooling the solvents were removed in vacuo and the residue dissolved in ethyl acetate (40 mL) and washed with water (10 mL). The aqueous layer was extracted with ethyl acetate (40mL) and the combined organic extracts washed with brine (10 mL), dried (Na2SO4) and concentrated in vacuo. The crude product was chromatographed on "flash" silica gel with ethyl acetate: hexane (1:9, 1:4, 1:3) to afford 5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine as an oil, 218 mg, 59%.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 5 h
  3. temperatureAfter cooling the solvents
  4. customwere removed in vacuo
  5. dissolutionthe residue dissolved in ethyl acetate (40 mL)
  6. washwashed with water (10 mL)
  7. extractionThe aqueous layer was extracted with ethyl acetate (40mL)
  8. washthe combined organic extracts washed with brine (10 mL)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customThe crude product was chromatographed on "flash" silica gel with ethyl acetate: hexane (1:9, 1:4, 1:3)

出典と根拠

ORDレコード
ord-4f390f4378ff494d833b3c8ee7dd0b15
出典データセット
uspto-grants-1997_01
特許番号
US05594011

反応ノート

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