Benzyl Bromide → 4-[2-(Benzyloxy)ethyl]-2-(4-bromophenyl)-5-methyl-1,3-oxazole

HRID 1181023Notes

Reaction equation

HRID 1181023 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([O:15][CH2:14][CH2:13][C:11]1[N:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[O:9][C:10]=1[CH3:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 108805302-(2-(4-Bromophenyl)-5-methyloxazol-4-YL)ethanol

Product 1

HCID 179843944-[2-(Benzyloxy)ethyl]-2-(4-bromophenyl)-5-methyl-1,3-oxazoleYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol (3.17 g, 11.2 mmol) in DMF (25 mL) was treated with NaH (0.67 g, 60% oil dispersion) at 0° C. and stirred for 5 min. Benzyl bromide (2.90 g, 16.9 mmol) was added, and the resulting mixture was stirred at room temperature for 3 h. The reaction was quenched with water, and the mixture was extracted with EtOAc (2×150 mL). The combined organics were dried (Na2SO4), concentrated, and purified by silica gel chromatography column (10% EtOAc/hexanes) to yield the title compound as an oil (2.50 g, 60%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 h
  2. customThe reaction was quenched with water
  3. extractionthe mixture was extracted with EtOAc (2×150 mL)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography column (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2fcfbd49da5e4eee8d70dd4d425a1f9d
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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