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

HRID 612925Notes

Reaction equation

HRID 612925 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
5 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-bc24e459eeba469f8131e8bc7072edc3
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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