HCID 17861257, compound → HCID 68884209, compound

HRID 1294207Notes

Reaction equation

HRID 1294207 reaction equation
C([O:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[CH:11][CH:10]=1)C1C=CC=CC=1>[C].[Pd].O1CCCC1>[CH3:20][C:19]1[O:18][C:17]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:16][C:15]=1[CH2:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 17861257HCID 17861257, compound

Product 1

HCID 68884209HCID 68884209, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-chloromethyl-5-methyl-2-phenyloxazole (20.18 g), 4-benzyloxyphenol (17.70 g), anhydrous potassium carbonate (12.22 g) and N,N-dimethylformamide (200 mL) was stirred at 90° C. for 15 hrs. The reaction mixture was poured into water, and the precipitated solid was collected by filtration, and dried with air to give crystals (29.03 g, 88%) of 4-[(4-benzyloxyphenoxy)methyl]-5-methyl-2-phenyloxazole. Recrystallization from ethyl acetate-hexane gave colorless leaflet crystals. melting point: 126-127° C. A mixture of the obtained 4-[(4-benzyloxyphenoxy)methyl]-5-methyl-2-phenyloxazole (22.6 g), 5% palladium carbon (10.0 g) and tetrahydrofuran (300 mL) was subjected to catalytic hydrogenation at room temperature and 1 atm. After filtering off the catalyst, the solvent was evaporated under reduced pressure to give crystals (16.3 g, 95%) of 4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenol. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 168-169° C.

Workup

  1. customRecrystallization from ethyl acetate-hexane
  2. customgave colorless leaflet crystals
  3. customwas subjected to catalytic hydrogenation at room temperature
  4. filtrationAfter filtering off the catalyst
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2e52a14c37b74449ab6096b1d69ffafc
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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