Potassium Carbonate → 2-(1,3-Dioxolan-2-yl)-6-methylpyridine 1-oxide

HRID 1258580Notes

Reaction equation

HRID 1258580 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1.C1C=C(Cl)C=C(C(OO)=[O:21])C=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N+:7]=1[O-:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 27343042-(1,3,-Dioxolan-2-yl)-6-methylpyridine

Product 1

HCID 671899662-(1,3-Dioxolan-2-yl)-6-methylpyridine 1-oxideYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution 2-(1,3-dioxolan-2-yl)-6-methylpyridine (3.7 g, 15.67 mmol, 1 eq.) in 200 ml of DCM was added mCPBA (7.21 g, 31.35 mmol, 2 eq.) portionwise (exotherm 20° C.>26° C.). The reaction was stirred for 1 hr and 100 ml of 2M aqueous K2CO3 solution was added. The mixture was stirred for 15 mins and the organic layer was separated, washed with water (100 ml), dried over MgSO4 and evaporated to give 2-(1,3-dioxolan-2-yl)-6-methylpyridine 1-oxide (2.4 g, 80% yield) as a yellow liquid.

Workup

  1. stirringThe mixture was stirred for 15 mins
  2. customthe organic layer was separated
  3. washwashed with water (100 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-2bc57693ea5e458bb7b80e05fb4286e2
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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