1,3-Dibromopropane → 3-(3-Bromopropyl)-5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-oxadiazol-2(3H)-one
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[O:20][C:19](=[O:21])[NH:18][N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[Br:28][CH2:29][CH2:30][CH2:31]Br>CN(C)C=O>[Br:28][CH2:29][CH2:30][CH2:31][N:18]1[N:17]=[C:16]([C:7]2[CH:8]=[C:9]([C:12]([CH3:14])([CH3:15])[CH3:13])[C:10]([OH:11])=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=2)[O:20][C:19]1=[O:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-oxadiazol-2(3H)-one (0.50 g) in dimethylformamide (8 ml) were added sodium carbonate (0.36 g) and 1,3-dibromo-propane (1.74 g), followed by stirring at room temperature for 5 hours. After completion of the reaction, the reaction mixture was poured into ice-water, and the product was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform) and then recrystallized from chloroform/n-hexane to afford 0.45 g (63%) of the title compound as colorless crystals. mp 130-131° C. NMR (CDCl3) (200 MHz) δ: 1.46 (18H, s), 2.1-2.6 (2H, m), 3.46 (2H, t, J=6.6 Hz), 3.93 (2H, t,J=6.6 Hz), 5.60 (1H, s), 7.63 (2H, s)
Workup
- customAfter completion of the reaction
- extractionthe product was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluent; chloroform)
- customrecrystallized from chloroform/n-hexane
Sources & evidence
- ORD record
- ord-c6ceab8309fc421aa2d20459064a55df
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998452
Reaction notes
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