tert-Butyl hydroperoxide → HCID 15008719, compound

HRID 1087943Notes

Reaction equation

HRID 1087943 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[N:5]=1)([CH3:3])=[CH2:2].[Cl:12]N1C(=O)CCC1=O.C(OO)(C)(C)C>C(Cl)(Cl)(Cl)Cl>[Cl:12][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[N:5]=1)=[CH2:3]

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 31398ChlorosuccinimideHCID 22164295HCID 22164295, compound

Product 1

HCID 15008719HCID 15008719, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 13.6 g of 2-isopropenyl-6-methoxypyridine, 16.3 g of N-chlorosuccinimide, 0.2 g of t-butylhydroperoxide and 30 ml of carbon tetrachloride was stirred at 140° 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 1:25) to obtain the following three fractions: 4.75 g of a first fraction (objective product/byproduct=0.2), 5.99 g of a second fraction (objective product/byproduct=0.714) and 0.41 g of a third fraction (objective product=1.0).

Workup

  1. customwhile being irradiated with light
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. filtrationthe insoluble matter was filtered out
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate-n-hexane 1:25)
  6. customto obtain the following three fractions

Sources & evidence

ORD record
ord-942239d596a6453290932c04e7a26275
Source dataset
uspto-grants-1990_10
Patent number
US04960897

Reaction notes

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