Sodium Hypochlorite → HCID 57827258, compound
Reaction equation
Cl[O-].[Na+].[CH3:4][O:5][CH:6]([CH2:11][CH:12]=[CH2:13])[CH2:7][CH:8]=[N:9][OH:10]>ClCCl>[CH3:4][O:5][CH:6]1[CH2:7][C:8]2=[N:9][O:10][CH2:13][CH:12]2[CH2:11]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A sodium hypochlorite solution (5% available chlorine, 9.36 mL) was added dropwise to a solution of 3-methoxy-5-hexenal oxime (450 mg) in dichloromethane (20 mL) at 0° C., and the mixture was stirred at 0° C. to room temperature for 1.5 hours. The reaction solution was poured into ice water, followed by extraction with dichloromethane. The extract was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under normal pressure. The resulting crude product was purified by silica gel column chromatography to obtain the less polar title compound (230 mg) and the more polar title compound (150 mg).
Workup
- extractionfollowed by extraction with dichloromethane
- washThe extract was washed with a saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- customThe drying agent was removed by filtration
- concentrationthe filtrate was concentrated under normal pressure
- customThe resulting crude product was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-45dfbab26ca34a0cb54a4adfd3c485c2
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946211B2
Reaction notes
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