Sodium ethanethiolate → Methyl 4-[3-(ethylthio)propyl]bicyclo[2.2.2]octane-1-carboxylate
Reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([O:19][CH3:20])=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)(=O)=O.[CH2:21]([S-:23])[CH3:22].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:21]([S:23][CH2:6][CH2:7][CH2:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([O:19][CH3:20])=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)[CH3:22]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 45 °C
Procedure
Mesylate 11-5 (3.30 g, 10.9 mmol) was dissolved in DMF (20 mL) and treated with sodium ethanethiolate (1.82 g, 21.7 mmol). The solution was stirred at 45° C. for 3 h, then the mixture was diluted with 100 mL of ethyl acetate and washed twice with 1N aqueous HCl, then with saturated aqueous sodium bicarbonate, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated to afford methyl 4-[3-(ethylthio)propyl]bicyclo[2.2.2]octane-1-carboxylate (11-6) as a crude oil which was used without purification in the next step.
Workup
- washwashed twice with 1N aqueous HCl
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-af2cecdb19664bf285599a4ff49c08f1
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504402B2
Reaction notes
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