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

HRID 2299831Notes

Reaction equation

HRID 2299831 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-b38b886f870b4357aca3eb5cd68195fc
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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