Sodium hydride → 8-(2-Methylbenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine

HRID 4305

반응식

HRID 4305 반응식
[H-].[Na+].[I-].[CH3:4][C:5]1[CH:27]=[CH:26][CH:25]=[CH:24][C:6]=1[CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][N+](C)(C)C)=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1>C(O)C#C>[CH3:4][C:5]1[CH:27]=[CH:26][CH:25]=[CH:24][C:6]=1[CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][O:8][CH2:7][C:6]#[CH:5])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 138259408-(2-Methylbenzyloxy)-3-trimethylammoniomethyl-2-methylimidazo[1,2-a]pyridine iodide

생성물 1

HCID 138259168-(2-Methylbenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine수율 110.8%

시약·촉매·용매 1

HCID 7859Propargyl alcohol용매

실험 절차

To a solution of sodium hydride (63.6% in mineral oil dispersion, 0.285 g) in 2-propynyl alcohol (12 ml) was added 8-(2-methylbenzyloxy)-3-trimethylammoniomethyl-2-methylimidazo[1,2-a]pyridine iodide (3 g) and the mixture was heated at 85°-100° C. for 1.5 hours. After being cooled, the mixture was poured into ice-water and the resulting precipitate was collected by filtration and dissolved in methylene chloride. The solution was treated successively with silica gel (4.5 g) and activated charcoal and evaporated in vacuo. The crystalline residue was recrystallized from a mixture of ethyl acetate and petroleum ether to give 8-(2-methylbenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine (1.18 g).

후처리

  1. temperaturethe mixture was heated at 85°-100° C. for 1.5 hours
  2. temperatureAfter being cooled
  3. filtrationthe resulting precipitate was collected by filtration
  4. dissolutiondissolved in methylene chloride
  5. additionThe solution was treated successively with silica gel (4.5 g) and activated charcoal
  6. customevaporated in vacuo
  7. customThe crystalline residue was recrystallized from a mixture of ethyl acetate and petroleum ether

출처 및 근거

ORD 기록
ord-ff349a1b204b4c2aab891a575c293bf5
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725601

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