m-Chloroperbenzoic acid → 2-Methyl-5-[(oxiran-2-yl)methoxy]-1-oxo-1lambda~5~-pyridine

HRID 1701765Notes

Reaction equation

HRID 1701765 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[O:12]1[CH2:23][CH:13]1[CH2:14][O:15][C:16]1[CH:17]=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=1>ClCCl>[O:12]1[CH2:23][CH:13]1[CH2:14][O:15][C:16]1[CH:17]=[N+:18]([O-:9])[C:19]([CH3:22])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 222202352-Methyl-5-[(oxiran-2-yl)methoxy]pyridine

Product 1

HCID 204834682-Methyl-5-[(oxiran-2-yl)methoxy]-1-oxo-1lambda~5~-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 12.2 g of m-chloroperbenzoic acid in 100 ml of dichloromethane is added dropwise over the course of approx. 10 minutes, whilst stirring, to a solution of 10 g of crude 3-(2,3-epoxy-propoxy)-6-methyl-pyridine in 100 ml of dichloromethane, the temperature of the solution rising to 32° C. The reaction mixture is stirred for a further 30 minutes and is then extracted with 40 ml of saturated potassium bicarbonate solution, dried and evaporated in vacuo. 3-(2,3-Epoxy-propoxy)-6-methylpyridine-1-oxide, thus obtained, is used further in the crude state.

Workup

  1. customrising to 32° C
  2. extractionis then extracted with 40 ml of saturated potassium bicarbonate solution
  3. customdried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-88649c03da434d95bd5f68506834564d
Source dataset
uspto-grants-1980_03
Patent number
US04195090

Reaction notes

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