Dimethylformamide → ethyl (6E)-6-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-6-phenylhexanoate

HRID 1070187Notes

Reaction equation

HRID 1070187 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8].[OH:14][C:15]1[CH:39]=[CH:38][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)\[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.CCCCCC.O>[O:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:5]1[O:6][C:7]([CH3:8])=[C:3]([CH2:2][O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)\[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:38][CH:39]=2)[N:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11089565ethyl (6E)-6-[(4-hydroxyphenyl)methoxyimino]-6-phenylhexanoateHCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazole

Product 1

HCID 11135070ethyl (6E)-6-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-6-phenylhexanoateYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 4-chloromethyl-2-(2-furyl)-5-methyloxazole (368 mg), ethyl E-6-(4-hydroxybenzyloxyimino)-6-phenylhexanoate (600 mg), potassium carbonate (467 mg) and N,N-dimethylformamide (7 ml) was stirred at room temperature for 13 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-6-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxyimino]-6-phenylhexanoate (770 mg, yield 88%) as a colorless oil from an ethyl acetate-hexane (2:7, 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-ac8ed704e59442d387109a648b012bef
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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