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

HRID 2254780ノート

反応式

HRID 2254780 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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-oxazolecarboxylate in the form of yellow crystals of m.p. 109°-110°.

後処理

  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

出典と根拠

ORDレコード
ord-a26c95414d90447d8343ba7a884b5c62
出典データセット
uspto-grants-1993_08
特許番号
US05236952

反応ノート

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