Pivaloyl chloride → HCID 22182285, compound

HRID 900405Notes

Reaction equation

HRID 900405 reaction equation
[CH2:1]([O:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[NH+:8]([O-:13])[C:7]([CH3:15])([CH3:14])[CH2:6]1)[CH2:2][CH3:3].[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>C1(C)C=CC=CC=1.O.[Pt]>[CH3:18][C:17]([CH3:20])([CH3:19])[C:16]([O:13][N:8]1[C:7]([CH3:14])([CH3:15])[CH2:6][CH:5]([O:4][CH2:1][CH2:2][CH3:3])[CH2:10][C:9]1([CH3:12])[CH3:11])=[O:21]

Participants

6

Reactant 2

HCID 62493Pivaloyl chlorideHCID 86605514HCID 86605514, compound

Product 1

HCID 22182285HCID 22182285, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

21.4 g (0.1 mol) of 4-propoxy-2,2,6,6-tetramethylpiperidine N-oxide (for preparation, see DE-A4 219 459) are hydrogenated to saturation at 4 bar in 20 ml of toluene using 0.05 g of platinum (10% on carbon). The catalyst is filtered off and 13 g (0.108 mol) of pivaloyl chloride are slowly added dropwise to the colourless filtrate under nitrogen. After the slightly exothermic reaction has abated, the mixture is stirred for another 1 hour at room temperature and diluted with 20 ml of water. The organic phase is washed with 4% NaOH solution, dried over MgSO4 and freed of the toluene on a rotary evaporator. This gives 13.5 g (45%) of the compound 110 which is in the form of a colourless oil.

Workup

  1. filtrationThe catalyst is filtered off
  2. customAfter the slightly exothermic reaction
  3. washThe organic phase is washed with 4% NaOH solution
  4. dry with materialdried over MgSO4
  5. customfreed of the toluene on a rotary evaporator

Sources & evidence

ORD record
ord-21c464cabf374ae3902af9d1e6fadb12
Source dataset
uspto-grants-2008_04
Patent number
US07358365B2

Reaction notes

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