Sulfuric acid magnesium salt (1:1) → HCID 19828753, compound

HRID 1494673Notes

Reaction equation

HRID 1494673 reaction equation
[CH2:1]([C:7]12[S:14][CH2:13][C:10]([CH2:15][CH2:16][CH3:17])([CH2:11][S:12]1)[CH2:9][S:8]2=[O:18])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].S([O-])([O-])(=O)=[O:20].[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O>[CH2:1]([C:7]12[S:12][CH2:11][C:10]([CH2:15][CH2:16][CH3:17])([CH2:13][S:14]1)[CH2:9][S:8]2(=[O:20])=[O:18])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 19828749HCID 19828749, compound

Product 1

HCID 19828753HCID 19828753, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of 1-(hex-5-ynyl)-4-n-propyl-2,6,7-trithiabicyclo[2.2.2]octane-2-oxide (0.302 g.) in dry acetone (120 ml) containing anhydrous magnesium sulphate (0.75 g) at -20° C. was added a solution of potassium permanganate (0.24 g) in dry acetone (25 ml). The mixture was allowed to warm to 20° and stirred for 72 hours. The colourless mixture was filtered through kieselguhr and the solid residue was washed with acetone. The filtrates were evaporated in vacuo and a colourless solid residue was obtained. The residue was purified by chromatography on silica eluting with dichloromethane. 1-(Hex-5-ynyl)-4-n-propyl-2,6,7-trithiabicyclo[2.2.2]octane-2,2-dioxide was obtained as a colourless solid (100 mg).

Workup

  1. temperatureto warm to 20°
  2. filtrationThe colourless mixture was filtered through kieselguhr
  3. washthe solid residue was washed with acetone
  4. customThe filtrates were evaporated in vacuo
  5. customa colourless solid residue was obtained
  6. customThe residue was purified by chromatography on silica eluting with dichloromethane

Sources & evidence

ORD record
ord-efb4144d39d9471cb5dad1a95fd35fe8
Source dataset
uspto-grants-1991_06
Patent number
US05026874

Reaction notes

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