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2-Bromoethanol → 3-(2-Bromoethoxy)-5-phenylisoxazole

HRID 612925
ノート
印刷プレビュー

反応式

HRID 612925 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC([N+](C(OCC)=O)=[N-])=O)C.[OH:32][C:33]1[CH:37]=[C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:35][N:34]=1.[Br:44][CH2:45][CH2:46]O>C1(C)C=CC=CC=1>[Br:44][CH2:45][CH2:46][O:32][C:33]1[CH:37]=[C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:35][N:34]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 14357405DiethyldiazodicarboxylateHCID 178515569HCID 178515569、化合物

生成物 1

HCID 195964873-(2-Bromoethoxy)-5-phenylisoxazole収率 90.9%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
5 °C

実験手順

Triphenylphosphine (15.7 g) was dissolved in toluene (200 ml), and the solution was cooled to 5° C. Diethyldiazodicarboxylate (10.4 g) was added to the solution, and the resulting mixture was stirred at the same temperature for 10 minutes. Then, 3-hydroxy-5-phenylisoxazole (8.0 g) and 2-bromoethanol (7.5 g) were added in this order to the reaction mixture, followed by stirring of the resulting mixture at room temperature for 10 minutes and further at room temperature for 2 hours. Insolubles were filtered off from the mixture, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to obtain the title compound (12.1 g, 90%) as colorless crystals.

後処理

  1. stirringby stirring of the resulting mixture at room temperature for 10 minutes and further at room temperature for 2 hours
  2. filtrationInsolubles were filtered off from the mixture
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-bc24e459eeba469f8131e8bc7072edc3
出典データセット
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06005116

反応ノート

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