Water → 2-(4-Benzyloxyphenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole

HRID 322378Notes

Reaction equation

HRID 322378 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:6][CH:5]=1.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:33][CH:34]=[C:35]([CH2:37]Cl)[N:36]=2)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:33][CH:34]=[C:35]([CH2:37][O:3][C:4]3[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]4[CH:17]=[CH:16][N:15]=[CH:14]4)=[CH:6][CH:5]=3)[N:36]=2)=[CH:28][CH:27]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazoleHCID 220098452-(4-Benzyloxy-phenyl)-4-chloromethyl-oxazole

Product 1

HCID 220097222-(4-Benzyloxyphenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazoleYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (440 mg) was added, at room temperature, to a solution of 1-[3-(4-hydroxyphenyl)propyl]imidazole (2.02 g) in N,N-dimethylformamide (50 ml). The mixture was stirred for 1.5 hour, to which was added 2-(4-benzyloxyphenyl)-4-chloromethyloxazole (3.60 g). The mixture was stirred for further 3 hours at 80° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The residue was subjected to a silica gel column chromatography. A crystalline product obtained from the fraction eluted with ethyl acetate-methanol (50:1, v.v) was recrystallized from ethanol to give 2-(4-benzyloxyphenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole (2.88 g, 62%) as colorless prisms, mp 133-134° C.

Workup

  1. stirringThe mixture was stirred for further 3 hours at 80° C
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customA crystalline product obtained from the fraction
  7. washeluted with ethyl acetate-methanol (50:1, v.v)
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-2fc1cf8bc4c84ae1a9ac3d029d95f65e
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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