Dimethylformamide → ethyl (8E)-8-phenyl-8-[[4-[(5-phenyl-1,2,4-oxadiazol-3-yl)methoxy]phenyl]methoxyimino]octanoate

HRID 2299866Notes

Reaction equation

HRID 2299866 reaction equation
Cl[CH2:2][C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1.[OH:14][C:15]1[CH:41]=[CH:40][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.CCCCCC.O>[C:34]1(/[C:22](=[N:21]/[O:20][CH2:19][C:18]2[CH:40]=[CH:41][C:15]([O:14][CH2:2][C:3]3[N:7]=[C:6]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[O:5][N:4]=3)=[CH:16][CH:17]=2)/[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3021543-(Chloromethyl)-5-phenyl-1,2,4-oxadiazoleHCID 22344573ethyl (8E)-8-[(4-hydroxyphenyl)methoxyimino]-8-phenyloctanoate

Product 1

HCID 22344614ethyl (8E)-8-phenyl-8-[[4-[(5-phenyl-1,2,4-oxadiazol-3-yl)methoxy]phenyl]methoxyimino]octanoateYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 3-chloromethyl-5-phenyl-1,2,4-oxadiazole (335 mg), ethyl E-8-(4-hydroxybenzyloxyimino)-8-phenyloctanoate (600 mg), potassium carbonate (432 mg) and N,N-dimethylformamide (7 ml) was stirred at room temperature for 18 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl E-8-phenyl-8-[4-(5-phenyl-1,2,4-oxadiazol-3-ylmethoxy)benzyloxyimino]octanoate (267 mg, yield 32%) as a colorless oil from an ethyl acetate-hexane (1:5, v/v)-eluted fraction.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3d7101afffcf41eb941baa500ed9f9a6
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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