m-Chloroperbenzoic acid → 2-(1,4-Dioxaspiro[4.5]dec-8-yl)pyridine N-oxide

HRID 1637091Notes

Reaction equation

HRID 1637091 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:22]>C(Cl)(Cl)Cl>[O:1]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N+:12]=3[O-:22])[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 211876632-(1,4-Dioxaspiro[4.5]decan-8-yl)pyridine

Product 1

HCID 206685242-(1,4-Dioxaspiro[4.5]dec-8-yl)pyridine N-oxideYield 93.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To an ice cold solution of 3 g (13.68 mmol) of 2-(1,4-dioxaspiro[4.5]dec-8-yl)pyridine in chloroform (46 mL) was added 4.51 g (14.36 mmol) of meta-chloroperoxybenzoic acid (50-60%). The reaction mixture was stirred and allowed to come to room temperature over a four hour period. The volume of the reaction mixture was reduced by approximately 75% under reduced pressure and the residual material was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide solution. The organic phase was separated and washed with water and brine, then dried (sodium sulfate) and concentrated to yield 3 g of the product as an oil.

Workup

  1. customthe residual material was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide solution
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-852be09af8fe41e6a4607af44ec5a047
Source dataset
uspto-grants-2000_03
Patent number
US06037354

Reaction notes

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