tert-Butyl hydroperoxide → HCID 15008721, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:5]=[C:4]([Cl:11])[N:3]=1.[Cl:12]N1C(=O)CCC1=O.C(OO)(C)(C)C>>[Cl:12][CH2:9][C:8]([C:6]1[CH:7]=[C:2]([Cl:1])[N:3]=[C:4]([Cl:11])[CH:5]=1)=[CH2:10]Participants
4
Conditions
- Temperature
- 180 °C
Procedure
A mixture of 26.3 g of 2,6-dichloro-4-isopropenylpyridine, 33.4 g of N-chlorosuccinimide, 2 g of t-butylhydroperoxide and 30 ml of carbon tetrachrolide was stirred at 180° C. for 5 hours while being irradiated with light. After the reaction mixture was cooled to room temperature, the insoluble matter was filtered out. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (eluted with ethyl acetate-n-hexane 1:20) to obtain 9.86 g of the objective compound.
Workup
- customwhile being irradiated with light
- temperatureAfter the reaction mixture was cooled to room temperature
- filtrationthe insoluble matter was filtered out
- concentrationThe filtrate was concentrated under a reduced pressure
- customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate-n-hexane 1:20)
Sources & evidence
- ORD record
- ord-2f1730b0b53c4d99b3931cda891090a5
- Source dataset
- uspto-grants-1990_10
- Patent number
- US04960897
Reaction notes
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