Acetic Acid → Isopropyl 4-nitrobenzyl 2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene]malonate

HRID 1532746

반응식

HRID 1532746 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]([CH:20]=O)=[CH:18][CH:17]=1.[C:24]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)(=[O:32])[CH2:25][C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[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]=[C:25]([C:24]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=2)=[O:32])[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 107571064-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehydeHCID 220138954-Nitrobenzyl isopropyl malonate

생성물 1

HCID 70224823Isopropyl 4-nitrobenzyl 2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene]malonate수율 78.5%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (3.59 g, 11.7 mmol) synthesized according to the method described in WO95/18125 in toluene (40 ml) were added 4-nitrobenzyl isopropyl malonate (4 g, 14 mmol) obtained in Step 1, acetic acid (351 mg) and piperidine (498 mg). While removing water through Dean-Stark trap, the mixture was refluxed under heating. Two hours later, toluene was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=65:35) and the fraction containing the objective substance was concentrated under reduced pressure to give the title compound (5.24 g, yield 66%) as a yellow oil.

후처리

  1. customWhile removing water through Dean-Stark trap
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating
  4. customTwo hours later, toluene was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=65:35)
  6. additionthe fraction containing the objective substance
  7. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-39e17db1d5634eeb93f0a752e1d16511
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06204277B1

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