Potassium Carbonate → HCID 58381715, compound
Reaction equation
C(=O)([S:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH3:23])C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:4]([SH:3])[CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH3:23]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
S-(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenyl ethanethioate (7.00 g, 20.2 mmol) was dissolved in MeOH (100 mL) by stirring 10 minutes until the droplets of oil dissolved, before anhydrous potassium carbonate, K2CO3 (2.79 g, 20.2 mmol) was added in one portion. The mixture was stirred for 1 hour and 20 minutes at ambient temperature and quenched by addition of 1 M HCl (50 mL) and water (150 mL). The white cloudy mixture was added Et2O (250 mL) and the phases were separated. The water phase was extracted with Et2O (2×250 mL). The combined organic phases were washed with brine (250 mL) and dried (MgSO4). Filtration and evaporation gave the title compound as oil (5.99 g, 97% yield), which was used without further purification.
Workup
- additionwas added in one portion
- stirringThe mixture was stirred for 1 hour and 20 minutes at ambient temperature
- customquenched by addition of 1 M HCl (50 mL) and water (150 mL)
- additionThe white cloudy mixture was added Et2O (250 mL)
- customthe phases were separated
- extractionThe water phase was extracted with Et2O (2×250 mL)
- washThe combined organic phases were washed with brine (250 mL)
- dry with materialdried (MgSO4)
- filtrationFiltration and evaporation
Sources & evidence
- ORD record
- ord-16c188dbacfa4354b82fe5e19097bce1
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759558B2
Reaction notes
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