Hydrochloric Acid → ethyl (2Z)-2-(4-methoxyphenyl)-2-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]acetate

HRID 1070102Notes

Reaction equation

HRID 1070102 reaction equation
[H-].[Na+].[OH:3]/[N:4]=[C:5](/[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)\[C:6]([O:8][CH2:9][CH3:10])=[O:7].Cl[CH2:20][C:21]1[CH:40]=[CH:39][C:24]([O:25][CH2:26][C:27]2[N:28]=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:30][C:31]=2[CH3:32])=[CH:23][CH:22]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11](/[C:5](=[N:4]/[O:3][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:25][CH2:26][C:27]3[N:28]=[C:29]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[O:30][C:31]=3[CH3:32])=[CH:39][CH:40]=2)/[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 11770071ethyl (2Z)-2-hydroxyimino-2-(4-methoxyphenyl)acetate

Product 1

HCID 22344571ethyl (2Z)-2-(4-methoxyphenyl)-2-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]acetateYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 127 mg) was added under a nitrogen atmosphere to a solution of ethyl Z-2-hydroxyimino-2-(4-methoxyphenyl)acetate (711 mg) and 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (1.00 g) in N,N-dimethylformamide (10 ml) at room temperature and the mixture was stirred for 1 hour. After adding 1N HCl (5 ml), aqueous sodium bicarbonate was added, and then the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residue was subjected to column chromatography on silica gel to obtain ethyl Z-2-(4-methoxyphenyl)-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]acetate (1.50 g, yield: 94%) as crystals from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization was performed from ethyl acetate-hexane. m.p. 102-103° C.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5177867f09e54885ae62b7f688087b1c
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

Loading…