Ethyl 3-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-5-hydroxy-4,5-dihydroisoxazole-5-carboxylate → Ethyl 3-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]isoxazole-5-carboxylate

HRID 880369Notes

Reaction equation

HRID 880369 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]=1[C:33]1[CH2:37][C:36](O)([C:38]([O:40][CH2:41][CH3:42])=[O:39])[O:35][N:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]=1[C:33]1[CH:37]=[C:36]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[O:35][N:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 66758807Ethyl 3-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-5-hydroxy-4,5-dihydroisoxazole-5-carboxylate

Product 1

HCID 66759355Ethyl 3-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]isoxazole-5-carboxylateYield 79.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of ethyl 3-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-5-hydroxy-4,5-dihydroisoxazole-5-carboxylate (8.5 g, 14 mmol) and tosic acid hydrate (5.5 g, 29.5 mmol, 2.1 eq.) in toluene (150 mL) was refluxed for 6 hours. After cooling, the solution was washed with 1 M Na2CO3 solution then with brine. The solvent was removed and the residue was columned over a small pad of silica gel eluting with hexane/ethyl acetate 5/1 to provide the title compound (6.3 g, 79% yield).

Workup

  1. temperatureAfter cooling
  2. washthe solution was washed with 1 M Na2CO3 solution
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-68043b059fa9485ca8a8f58937ceb033
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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