1,5-Dibromopentane → 5-(2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy)pentylbromide

HRID 1294755Notes

Reaction equation

HRID 1294755 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][OH:15].[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.[OH-].[Na+].[Br-].C([NH+](CCCC)CCCC)CCC>CCOCC>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][Br:16]

Participants

6

Reactant 4

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanolHCID 13798051Tributylammonium bromide

Product 1

HCID 158961575-(2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy)pentylbromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The mixture of 2-(5-methyl-2-phenyloxazol-4-yl)ethanol (2.03 g), 1,5-dibromopentane (4.09 ml), 50% NaOH (4.0 ml) and tributylammonium bromide (0.1 g) was stirred at room temperature overnight. The reaction mixture was dilluted with ether, washed by water and an aqueous saturated solution of sodium chloride sucessively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1→4:1) to obtain the title compound (3.45 g) having the following physical data.

Workup

  1. washwashed by water
  2. dry with materialan aqueous saturated solution of sodium chloride sucessively, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1→4:1)

Sources & evidence

ORD record
ord-f2c3c1756c074451809b7c558ade060d
Source dataset
uspto-grants-2007_07
Patent number
US07241784B2

Reaction notes

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