Hydrochloric Acid → Ethyl 3-ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzoate

HRID 1295267Notes

Reaction equation

HRID 1295267 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([OH:15])[CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].Cl[CH2:17][C:18]1[N:19]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:21][C:22]=1[CH3:23].C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([O:15][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])[CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 22930676Ethyl 3-ethoxy-5-hydroxybenzoate

Product 1

HCID 22930682Ethyl 3-ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzoateYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 3-ethoxy-5-hydroxybenzoate (3.00 g), 4-chloromethyl-5-methyl-2-phenyloxazole (3.26 g), potassium carbonate (2.17 g) and N,N-dimethylformamide (60 ml) was stirred at 80° C. for 2 hrs. The reaction mixture was poured into water, acidified with 2N hydrochloric acid and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and ethyl 3-ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzoate (5.40 g, 99%) was obtained as an oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-86d2122280b2481ea5e519f642bc548d
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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