Pyridine → (trans)-3-(6-Phenyl-1,3,5-hexatriynyl)oxiranecarboxaldehyde

HRID 1906979ノート

反応式

HRID 1906979 の反応式
N1C=CC=CC=1.[C:7]1([C:13]#[C:14][C:15]#[C:16][C:17]#[C:18][C@@H:19]2[O:21][C@H:20]2[CH2:22][OH:23])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[C:7]1([C:13]#[C:14][C:15]#[C:16][C:17]#[C:18][C@@H:19]2[O:21][C@H:20]2[CH:22]=[O:23])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参加物

5

反応物 2

HCID 1049PyridineHCID 86740798(trans)-3-(6-Phenyl-1,3,5-hexatriynyl)oxiranemethanol

生成物 1

HCID 86740799(trans)-3-(6-Phenyl-1,3,5-hexatriynyl)oxiranecarboxaldehyde収率 43.7%

試薬・触媒・溶媒 2

HCID 10219390chromium (VI) trioxide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Chromium trioxide (951 mg, 9.51 mmole; dried in vacuo over phosphorous pentoxide) was added to a stirred solution of 1.49 g (18.88 mmole) of dry pyridine in 25 ml of dry methylene chloride. The deep red solution was stirred for 15 minutes at room temperature. A solution of (trans)-3-(6-phenyl-1,3,5-hexatriynyl)oxiranemethanol (300 mg, 1.35 mmole; see example 3) in 5 ml of dry methylene chloride was then added in one portion. A tarry, black deposit separated immediately. After stirring for 20 minutes at room temperature, the solution was decanted and filtered through a pad of silica gel. Several portions of ether were then passed through the silica gel. Solvent was removed from the combined filtrates and the residue was chromatographed on silica gel (ether-hexane) to afford 130 mg of the title compound.

後処理

  1. customA tarry, black deposit separated immediately
  2. stirringAfter stirring for 20 minutes at room temperature
  3. customthe solution was decanted
  4. filtrationfiltered through a pad of silica gel
  5. customSolvent was removed from the combined filtrates
  6. customthe residue was chromatographed on silica gel (ether-hexane)

出典と根拠

ORDレコード
ord-567c85d154994ac2b6dd91faebf61ce0
出典データセット
uspto-grants-1987_03
特許番号
US04654426

反応ノート

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