Dimethylformamide → methyl (4E)-4-[[4-[(5-methyl-2-phenyl-1,3-thiazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoate

HRID 1070158Notes

Reaction equation

HRID 1070158 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:6][C:7]=1[CH3:8].[OH:15][C:16]1[CH:37]=[CH:36][C:19]([CH2:20][O:21]/[N:22]=[C:23](/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)\[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.CCCCCC.O>[CH3:8][C:7]1[S:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][C:3]=1[CH2:2][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][O:21]/[N:22]=[C:23](/[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)\[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10946929methyl (4E)-4-[(4-hydroxyphenyl)methoxyimino]-4-phenylbutanoateHCID 12794636Thiazole, 4-(chloromethyl)-5-methyl-2-phenyl-

Product 1

HCID 11027498methyl (4E)-4-[[4-[(5-methyl-2-phenyl-1,3-thiazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoateYield 71.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 4-(chloromethyl)-5-methyl-2-phenylthiazol (394 mg), methy E-4-(4-hydroxybenzyloxyimino)-4-phenylbutyrate (500 mg), potassium carbonate (442 mg) and N,N-dimethyformamide (10 ml) was stirred at room temperature for 72 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was subjected to silica gel chromatography to obtain methy E-4-[4-(5-methyl-2-phenyl-4-thiazolylmethoxy) benzyloxyimino]-4-phenylbutyrate (570 mg, yield 71%) as a colorless oil from an ethyl acetate-hexane (1:5, v/v)-eluted fraction.

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-e2c6dee942e645b8889b329541247d89
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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