Water → HCID 19828747, compound

HRID 1494672Notes

Reaction equation

HRID 1494672 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][O:8]2)[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].C([O-])(=[O:20])C.[Na+].ClC1C=CC=C(C(OO)=O)C=1.O>C(#N)C>[CH2:1]([C:7]12[S:12][CH2:11][C:10]([CH2:15][CH2:16][CH3:17])([CH2:13][S:14]1=[O:20])[CH2:9][O:8]2)[CH2:2][CH2:3][CH2:4][C:5]#[CH:6]

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 517045Sodium AcetateHCID 193733381-(Hex-5ynyl)-4-n-propyl-2-oxa-6,7-dithiabicyclo[2.2.2]octane

Product 1

HCID 19828747HCID 19828747, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(hex-5-ynyl)-4-n-propyl-2-oxa-6,7-dithiabicyclo-[2.2.2]octane (0.75 g., 1 equivalent), anhydrous sodium acetate (2.0 g.) and 3-chloroperbenzoic acid (85%, 1.12 g. 2.5 equivalents) was stirred at 20° in dry acetonitrile (50 ml.) for 18 hours. Water was added and the mixture was extracted with ethyl acetate. The extracts were washed with sodium hydrogen carbonate solution, water and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo. After purification by chromatography on silica (eluting with ethyl acetate), 1-(hex-5-ynyl)-4-n-propyl-2-oxa-6,7-dithiabicyclo[2.2.2]octane-6-oxide was obtained as a colourless solid (0.35 g.).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extracts were washed with sodium hydrogen carbonate solution, water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customThe solvent was removed in vacuo
  5. customAfter purification by chromatography on silica (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-ac0bc5179ca14723a0dda94d72f5be67
Source dataset
uspto-grants-1991_06
Patent number
US05026874

Reaction notes

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