Ethyl orthoformate → 4-n-Propyl-2,6,7-trithiabicyclo[2.2.2]octane
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
Product 1
Reagents, catalysts & solvents 1
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
- additioncontaining Amberlyst "15" (1.0 g.)
- temperatureThe mixture was cooled
- filtrationfiltered
- customThe filtrates were evaporated in vacuo
- 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
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