Sodium Sulfite → 4-[2,2,2-trifluoro-1-(triethylsilyloxy)ethyl]pyridine N-oxide

HRID 1880761Notes

Reaction equation

HRID 1880761 reaction equation
[F:1][C:2]([F:19])([F:18])[CH:3]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[O:4][Si:5]([CH2:10][CH3:11])([CH2:8][CH3:9])[CH2:6][CH3:7].ClC1C=CC=C(C(OO)=[O:28])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[F:19][C:2]([F:18])([F:1])[CH:3]([C:12]1[CH:17]=[CH:16][N+:15]([O-:28])=[CH:14][CH:13]=1)[O:4][Si:5]([CH2:8][CH3:9])([CH2:6][CH3:7])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 595702944-[2,2,2-Trifluoro-1-(triethylsilyloxy)ethyl]pyridine

Product 1

HCID 595703784-[2,2,2-trifluoro-1-(triethylsilyloxy)ethyl]pyridine N-oxideYield 86.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To 40 ml of chloroform were added 5.5 g of 4-[2,2,2-trifluoro-1-(triethylsilyloxy)ethyl]pyridine, and 7.5 g of meta-chloroperbenzoic acid, and the mixture was stirred at 0° C. for 2 hours, and at room temperature for 3 hours. Thereafter, the reaction solution was poured into an aqueous saturated sodium sulfite solution, followed by extraction with chloroform three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 5 g of 4-[2,2,2-trifluoro-1-(triethylsilyloxy)ethyl]pyridine N-oxide.

Workup

  1. waitat room temperature for 3 hours
  2. extractionfollowed by extraction with chloroform three times
  3. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8472f885485a498c8d70d7349187b95d
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

Loading…