Methanol → HCID 68883448, compound

HRID 1294227Notes

Reaction equation

HRID 1294227 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:29]=[CH:30][CH:31]=1)[CH2:18][S:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([OH:25])=[O:24].S(=O)(=O)(O)O.[CH3:37]O>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:29]=[CH:30][CH:31]=1)[CH2:18][S:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([O:25][CH3:37])=[O:24]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 68887523HCID 68887523, compound

Product 1

HCID 68883448HCID 68883448, compoundYield 67%

Procedure

A mixture of 3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]benzoic acid (3.20 g), conc. sulfuric acid (1 mL) and methanol (50 mL) was stirred with heating under reflux for 1 hr. The reaction mixture was concentrated, water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]benzoate as an oil (2.20 g, yield 67%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d8205a3db1714932af751c55b9ec2b35
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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