Diethyl Ether → Ethyl 5-(2-methoxyphenyl)-2-isoxazoline-3-carboxylate

HRID 1734977Notes

Reaction equation

HRID 1734977 reaction equation
F[C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[CH:4]=[CH2:5].Cl[C:12](=[N:18][OH:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14].C[CH2:21][O:22]CC.C(N(CC)CC)C>O>[CH3:21][O:22][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[O:19][N:18]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:5]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 6816376Ethyl chloro(hydroximino)acetateHCID 202266752,4-Difluorostyrene

Product 1

HCID 19436742Ethyl 5-(2-methoxyphenyl)-2-isoxazoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4.2 g of 2,4-difluorostyrene and 4.55 g of ethyl 2-chloro-2-hydroximinoacetate are introduced into 350 ml of ether, and the mixture is cooled to 0° C. 3.03 g of triethylamine are added dropwise to this mixture at 0° C. The mixture is stirred for 3 hours at room temperature, 50 ml of water are then added, and the mixture is extracted using ether. After drying over MgSO4, the ether is distilled off, and the residue is purified over a silica column (eluent: n-heptane:ethyl acetate=8:2). This gave 6.68 g (86% of theory) of product of refractive index [n]D20 =1.5019.

Workup

  1. extractionthe mixture is extracted
  2. dry with materialAfter drying over MgSO4
  3. distillationthe ether is distilled off
  4. customthe residue is purified over a silica column (eluent: n-heptane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-f7a72826af974f848273800ccd5b9792
Source dataset
uspto-grants-1996_07
Patent number
US05536698

Reaction notes

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