4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[(E)-2-phenylethenyl]oxazole → 4-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-phenylethyl)oxazole

HRID 322388Notes

Reaction equation

HRID 322388 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:29]=[CH:28][C:12]([O:13][CH2:14][C:15]3[N:16]=[C:17](/[CH:20]=[CH:21]/[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:18][CH:19]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>C(O)C.[C].[Pd]>[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:29]=[CH:28][C:12]([O:13][CH2:14][C:15]3[N:16]=[C:17]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[O:18][CH:19]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 155216754-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[(E)-2-phenylethenyl]oxazole

Product 1

HCID 220097804-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-phenylethyl)oxazoleYield 57%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-[4-[3-(1-imidazolyl)propyl]-phenoxymethyl]-2-[(E)-2-phenylethenyl]oxazole (300 mg) in ethanol (100 ml) was added palladium-carbon (5%, wet, 300 mg). The mixture was subjected to catalytic hydrogenation at room temperature under atmospheric pressure. The catalyst was filtered off. The filtrate was concentrated to leave a crystalline product, which was recrystallized from ethyl acetate-hexane to give 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(2-phenylethyl)oxazole (170 mg, 57%) as colorless prisms, mp 67-68° C.

Workup

  1. customwas subjected to catalytic hydrogenation at room temperature under atmospheric pressure
  2. filtrationThe catalyst was filtered off
  3. concentrationThe filtrate was concentrated
  4. customto leave a crystalline product, which
  5. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a863f5fca8444503a3d23ed08552179a
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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