3-Bromo-1-propanol → 3-[(4,6-Diphenyl-2-pyridyl)oxy]-1-propanol

HRID 2380331Notes

Reaction equation

HRID 2380331 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10][C:9](=[O:19])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][CH2:23][OH:24]>C(=O)([O-])[O-].[Ag+2].C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:10]=[C:9]([O:19][CH2:21][CH2:22][CH2:23][OH:24])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 123083-Bromo-1-propanolHCID 38462014,6-Diphenyl-2-pyridone

Product 1

HCID 189872833-[(4,6-Diphenyl-2-pyridyl)oxy]-1-propanol

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

The procedure in Example 4 is followed but using 4,6-diphenyl-2-pyridone (15 g), freshly distilled 3-bromo-1-propanol (16.5 cc), silver carbonate (8.4 g) and toluene (600 cc). The reaction mixture is refluxed for 144 hours. The product is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 7-3). (white solid; m.p.=94° C.)

Workup

  1. temperatureThe reaction mixture is refluxed for 144 hours
  2. customThe product is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 7-3)

Sources & evidence

ORD record
ord-4759aa999f6745418688925152ff27e7
Source dataset
uspto-grants-1994_11
Patent number
US05366982

Reaction notes

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