2-(3-benzyloxyphenyl)-4,5-dihydro-4(R)-phenyloxazole → (R)-3-(4-Phenyl-4,5-dihydrooxazol-2-yl)phenol

HRID 2395377Notes

Reaction equation

HRID 2395377 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[O:16][CH2:17][C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:19]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:15]2[O:16][CH2:17][C@@H:18]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:19]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 186655522-(3-benzyloxyphenyl)-4,5-dihydro-4(R)-phenyloxazole

Product 1

HCID 18665562(R)-3-(4-Phenyl-4,5-dihydrooxazol-2-yl)phenolYield 48.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(3-Benzyloxyphenyl)-4,5-dihydro-4(R)-phenyloxazole (3 g, 8.9 mmol) was dissolved in ethyl acetate (15 ml) and hydrogenolyzed in the presence of 10% palladium-on-charcoal (300 mg). Recrystallization from ethyl acetate/n-hexane gave 4,5-dihydro-2-(3-hydroxyphenyl)-4(R)-phenyloxazole (1.03 g, 48% ) as colorless needles.

Workup

  1. customRecrystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-62991a0a54d641febc5c977efbd66948
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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