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

HRID 612925
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HRID 612925 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 14357405DiethyldiazodicarboxylateHCID 178515569HCID 178515569, 화합물

생성물 1

HCID 195964873-(2-Bromoethoxy)-5-phenylisoxazole수율 90.9%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
5 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bc24e459eeba469f8131e8bc7072edc3
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06005116

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