Sulfuric Acid → 2-[5-Hydroxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetonitrile

HRID 1294108Notes

Reaction equation

HRID 1294108 reaction equation
COC[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[N:25]=[C:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[O:27][C:28]=3[CH3:29])=[CH:18][CH:17]=2)=[C:9]([CH2:11][C:12]#[N:13])[CH:10]=1.S(=O)(=O)(O)O.O1CCCC1>O>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]3[N:25]=[C:26]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[O:27][C:28]=3[CH3:29])=[CH:20][CH:21]=2)=[C:9]([CH2:11][C:12]#[N:13])[CH:10]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 688858772-[5-Methoxymethoxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetonitrile

Product 1

HCID 688862422-[5-Hydroxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetonitrileYield 68.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-[5-methoxymethoxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetonitrile (1.83 g), 10% sulfuric acid (5 mL) and tetrahydrofuran (50 mL) was heated under reflux for 3 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give crystals (1.13 g, 68%) of 2-[5-hydroxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetonitrile. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 185-186° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b2e7532e001348258aa420e4a8004f46
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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