Formic Acid → 4-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde

HRID 4409

반응식

HRID 4409 반응식
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#N)=[CH:18][CH:17]=1.C(O)=[O:25]>[Ni]>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:25])=[CH:18][CH:17]=1

참가 물질

4

반응물 2

HCID 284Formic AcidHCID 137139704-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzonitrile

생성물 1

HCID 107571064-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde수율 78.5%

시약·촉매·용매 1

HCID 935Nickel촉매

실험 절차

A mixture of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzonitrile (6.5 g), Raney nickel alloy (6.5 g) and 70% formic acid (100 ml) was heated under reflux for 2 hours. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The remaining oily material was chromatographed on a column of silica gel, and from the fractions eluted with chloroform-hexane (1:1, V/V), there were obtained crystlas (5.2 g, 78.5%) of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde. Recrystallization from ether-hexane yielded colorless needles, m.p. 82°-84° C. Elemental analysis for C19H17NO3 ; Calcd.: C, 74.25; H, 5.57; N, 4.56. Found: C, 74.47; H, 5.53; N, 4.34.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe insoluble matter was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe remaining oily material was chromatographed on a column of silica gel
  11. washfrom the fractions eluted with chloroform-hexane (1:1, V/V)

출처 및 근거

ORD 기록
ord-02ae9b80d0de45e4bc6c27c8e8753812
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725610

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