m-Chloroperbenzoic acid → 2-[2-[(6-Bromohexyl)oxy]ethyl]pyridine N-oxide
Reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1>ClCCl>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N+:23]=1[O-:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
m-Chloroperbenzoic acid (1.13 g) was added in one portion to a solution of 2-[2-[(6-bromohexyl)oxy]ethyl]pyridine (1.0 g) in dichloromethane (50 ml). The solution was stirred at room temperature overnight. The mixture was quenched with 10% w/v sodium sulphite solution (50 ml) and the organic layer washed with 8% sodium bicarbonate solution (50 ml). The organic layer was dried and evaporated to leave the title compound as a pale yellow oil (980 mg) used without further purification. A portion (100 mg) was purified by FCC eluting with System A (80:20:1) to give a pale yellow oil (20 mg), t.l.c. (System A 80:20:1) Rf 0.48.
Workup
- customThe mixture was quenched with 10% w/v sodium sulphite solution (50 ml)
- washthe organic layer washed with 8% sodium bicarbonate solution (50 ml)
- customThe organic layer was dried
- customevaporated
Sources & evidence
- ORD record
- ord-87008fe0ad7145a5b223439de1f892ae
- Source dataset
- uspto-grants-1990_06
- Patent number
- US04937251
Reaction notes
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