Ethyl orthoformate → 4-n-Propyl-2,6,7-trithiabicyclo[2.2.2]octane

HRID 1494667Notes

Reaction equation

HRID 1494667 reaction equation
[SH:1][CH2:2][C:3]([CH2:8][CH2:9][CH3:10])([CH2:6][SH:7])[CH2:4][SH:5].[CH:11](OCC)(OCC)OCC>C1C=CC=CC=1>[CH2:8]([C:3]12[CH2:6][S:7][CH:11]([S:5][CH2:4]1)[S:1][CH2:2]2)[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 193732862-Mercaptomethyl-2-n-propylpropan-1,3-dithiol

Product 1

HCID 193734094-n-Propyl-2,6,7-trithiabicyclo[2.2.2]octane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Mercaptomethyl-2-n-propylpropan-1,3-dithiol (4.0 g.) and triethyl orthoformate (3.6 g.) were refluxed, with stirring, in dry benzene (120 ml.) containing Amberlyst "15" (1.0 g.). The mixture was cooled and filtered. The filtrates were evaporated in vacuo and the residue was purified by chromatography on alumina eluting with 1:10, dichloromethane: hexane saturated with ammonia. 4-n-Propyl-2,6,7-trithiabicyclo[2.2.2]octane was obtained as a colourless solid (3.1 g., m.pt. 139°).

Workup

  1. additioncontaining Amberlyst "15" (1.0 g.)
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customThe filtrates were evaporated in vacuo
  5. customthe residue was purified by chromatography on alumina eluting with 1:10, dichloromethane

Sources & evidence

ORD record
ord-6f226eda447f4b4ca2c0a26702c6c37b
Source dataset
uspto-grants-1991_06
Patent number
US05026874

Reaction notes

Loading…