Sulfuric Acid → 2-Phenyl-5-propyl-4-oxazolylmethanol

HRID 1294161Notes

Reaction equation

HRID 1294161 reaction equation
COC[O:4][CH2:5][C:6]1[N:7]=[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:9][C:10]=1[CH2:11][CH2:12][CH3:13].S(=O)(=O)(O)O.O1CCCC1>C(OCC)(=O)C>[C:14]1([C:8]2[O:9][C:10]([CH2:11][CH2:12][CH3:13])=[C:6]([CH2:5][OH:4])[N:7]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 17861363HCID 17861363, compound

Product 1

HCID 178612102-Phenyl-5-propyl-4-oxazolylmethanolYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methoxymethoxymethyl-2-phenyl-5-propyloxazole (2.64 g), 10% sulfuric acid (10 mL) and tetrahydrofuran (100 mL) was heated under reflux for 24 hrs. To the reaction mixture was added ethyl acetate, and the mixture was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated to give (2-phenyl-5-propyl-4-oxazolyl)methanol as a colorless oil (2.10 g, 96%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hrs
  3. washthe mixture was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a270043977b54c39a7cd4dc0e39d490f
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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