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

HRID 432882Notes

Reaction equation

HRID 432882 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 diluted 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-be45c0d5ab8d4d64a1a4a8d2b29204c0
Source dataset
uspto-grants-2003_12
Patent number
US06664281B1

Reaction notes

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