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

HRID 280398노트

반응식

HRID 280398 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 10219390chromium (VI) trioxide촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-244cbd15584340dd8a0a0f4fe21a22ef
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588828

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