Triethylamine → Ethyl 5-(3,4-dimethoxy-5-nitrophenyl)-4-oxazolecarboxylate

HRID 274508노트

반응식

HRID 274508 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[N+:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])#[C-:18].C(N(CC)CC)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[O:7][CH:18]=[N:17][C:19]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 533707Ethyl isocyanoacetateHCID 219286153,4-Dimethoxy-5-nitrobenzoyl chloride

생성물 1

HCID 21459162Ethyl 5-(3,4-dimethoxy-5-nitrophenyl)-4-oxazolecarboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2.5 g of 3,4-dimethoxy-5-nitrobenzoyl chloride in 10 ml of absolute tetrahydrofuran is treated with 1.1 ml of ethyl isocyanoacetate and subsequently with a solution of 3.0 ml of triethylamine in 10 ml of tetrahydrofuran and stirred at room temperature for 48 hours. After distillation of the solvent, the residue is extracted with ethyl acetate/water. The crude product obtained after evaporation is chromatographed on a 20-fold amount of silica gel with ethyl acetate. After recrystallization from ethyl acetate/hexane there is obtained ethyl 5-(3,4-dimethoxy-5-nitrophenyl)-4-oxazole-carboxylate in the form of yellow crystals of m.p. 109°-110°.

후처리

  1. distillationAfter distillation of the solvent
  2. extractionthe residue is extracted with ethyl acetate/water
  3. customThe crude product obtained
  4. customafter evaporation
  5. customis chromatographed on a 20-fold amount of silica gel with ethyl acetate
  6. customAfter recrystallization from ethyl acetate/hexane there

출처 및 근거

ORD 기록
ord-fb5dacd67b3d4d14aa57d5b2b8c451ba
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389653

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