Sodium hydride → 5-Ethynyl-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine

HRID 1489408

反応式

HRID 1489408 の反応式
O[C:2](C)(C#C)[CH2:3][C:4]1[CH:5]=[C:6]([CH:10]2[N:14]([CH3:15])[C:13](=[O:16])[CH2:12][CH2:11]2)[CH:7]=[N:8][CH:9]=1.[H-].[Na+].C1(C)C=CC=CC=1.CC(C)=O>C1(C)C=CC=CC=1>[C:3]([C:4]1[CH:5]=[C:6]([CH:10]2[N:14]([CH3:15])[C:13](=[O:16])[CH2:12][CH2:11]2)[CH:7]=[N:8][CH:9]=1)#[CH:2]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 196943255-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-methyl-5-pyrrolidin-2-onyl)pyridineHCID 20247278Toluene acetone

生成物 1

HCID 196943515-Ethynyl-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine収率 81.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
25 °C

実験手順

5-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine (200 mg, 0.77 mmol) was dissolved in toluene (20 mL) and catalytic sodium hydride (5 mg) was added. The solution was heated until several milliliters of toluene-acetone mixture were removed by distillation. The mixture was cooled to 25° C. and water (10 mL) and ethyl acetate (20 mL) were added. The organic phase was separated and the aqueous layer extracted with ethyl acetate (2×20 mL) and the combined organic extracts were washed with brine (10 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by silica gel column chromatography with ethyl acetate as eluant to afford 5-ethynyl-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine as a solid (125 mg, 81%). M.p. 83°-84° C.; 1H NMR (CDCl3, 300 MHz): δ 8.69 (d, J=2 Hz, 1H), 8.46 (d, J=2 Hz, 1H), 7.62 (t, J=2 Hz, 1H), 4.57 (dd, J=7, 6 Hz, 1H), 3.28 (s, 1H), 2.70 (s, 3H), 2.45-2.65 (m, 3H), 1.88 (m, 1H).

後処理

  1. customwere removed by distillation
  2. additionwater (10 mL) and ethyl acetate (20 mL) were added
  3. customThe organic phase was separated
  4. extractionthe aqueous layer extracted with ethyl acetate (2×20 mL)
  5. washthe combined organic extracts were washed with brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel column chromatography with ethyl acetate as eluant

出典と根拠

ORDレコード
ord-f249e497a3a94dfa8f5735dabae11bfc
出典データセット
uspto-grants-1997_10
特許番号
US05677459

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