Water → HCID 12565416, compound

HRID 895645Notes

Reaction equation

HRID 895645 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][O:14]C=O)=[CH:9][CH:8]=2)=[N:3]1.[OH-].[Na+].O>CO>[CH3:1][C:2]1([CH3:17])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=2)=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22380609HCID 22380609, compound

Product 1

HCID 12565416HCID 12565416, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4,4-Dimethyloxazolin-2-yl)-1-(formyloxymethyl)benzene (37 mg) was dissolved in methanol (0.4 ml), added with 1 N aqueous sodium hydroxide (0.18 ml) and stirred at room temperature for 20 minutes. The reaction mixture was added with water (5 ml) and extracted twice with ethyl acetate (5 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=1:2) to obtain 17.7 mg of the title compound. Yield: 54%.

Workup

  1. extractionextracted twice with ethyl acetate (5 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-37ca3c39d5f244f8b005853afc44f74a
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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