m-Chloroperbenzoic acid → HCID 19828749, compound

HRID 1494668Notes

Reaction equation

HRID 1494668 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)[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].ClC1C=CC=C(C(OO)=[O:26])C=1.C([O-])(=O)C.[Na+]>C(#N)C>[CH2:1]([C:7]12[S:12][CH2:11][C:10]([CH2:15][CH2:16][CH3:17])([CH2:9][S:8]1)[CH2:13][S:14]2=[O:26])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 517045Sodium AcetateHCID 19373275HCID 19373275, compound

Product 1

HCID 19828749HCID 19828749, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(hex-5-ynyl)-4-n-propyl-2,6,7-trithiabicyclo [2.2.2]octane (1.07 g. 1.0 equivalent), 3-chloroperbenzoic acid (0.80 g., 1.05 equivalent, 85% Lancaster Synthesis), and anhydrous sodium acetate (1.0 g.) in anhydrous acetonitrile was stirred at 20° from 24 hours. The solvent was removed in vacuo and the residue partitioned between water and ethyl acetate. The organic phase was separated, washed with sodium hydrogen carbonate solution and brine before drying over anhydrous magnesium sulphate. The solvent was removed in vacuo and the residue was chromatographed on silica. Elution with hexane: ethyl acetate mixtures (20% 75%) ethyl acetate gave 1-(hex-5-ynyl)-4-n-propyl-2,6,7-trithiabicyclo[ 2.2.2]octane 2-oxide as a colourless solid (0.47 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between water and ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with sodium hydrogen carbonate solution and brine
  5. dry with materialbefore drying over anhydrous magnesium sulphate
  6. customThe solvent was removed in vacuo
  7. customthe residue was chromatographed on silica
  8. washElution with hexane

Sources & evidence

ORD record
ord-7115cd3abb244b2baf4abc7861ff90c1
Source dataset
uspto-grants-1991_06
Patent number
US05026874

Reaction notes

Loading…