Ethylene Glycol → HCID 54000011, compound

HRID 279457Notes

Reaction equation

[CH2:1]([OH:4])[CH2:2]O.C1C=CC=CC=1.[CH3:11][C:12]1[CH:13]=[C:14]([CH:29]=[CH:30][CH:31]=1)[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[N:26][O:27][CH3:28])[C:24]#[N:25].NCCO>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C(OCC)(=O)C>[CH3:28][O:27][N:26]=[C:23]([C:24]1[O:4][CH2:1][CH2:2][N:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:14]1[CH:29]=[CH:30][CH:31]=[C:12]([CH3:11])[CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethylene glycol (2 ml) and benzene (10 ml) were added to 2-(3-methylphenoxymethyl)-α-methoxyiminophenyl acetonitrile (1.0 g, 3.6 mmol), 2-aminoethanol (400 mg, 6.6 mmol) and zinc acetate dihydrate (100 mg, 0.46 mmol), and the mixture was subjected to azeotropic dehydration and stirred at 100° C. for 20 hours. After allowing the mixture to stand for cooling, ethyl acetate was added to the reaction mixture. The mixture was washed successively with water and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give 2-(3-methylphenoxymethyl)phenyl 2-oxazolin-2-yl ketone O-methyloxime (280 mg,24%) as an oil.

Workup

temperaturefor cooling
washThe mixture was washed successively with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane)

Sources & evidence

ORD record: ord-709a60e27cf64900a1e9998802d06f7d
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362212B1

Reaction notes

Loading…