Iodine → HCID 70244124, compound
Reaction equation
[C:1]1([S:7]([O-:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].II.[CH2:13]([C:16](=[CH2:21])[C:17]([O:19][CH3:20])=[O:18])[CH2:14][CH3:15].C(N(CC)CC)C>O.ClCCl>[CH3:20][O:19][C:17](=[O:18])/[C:16](/[CH2:13][CH2:14][CH3:15])=[CH:21]/[S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]Participants
Conditions
- Temperature
- 0 °C
Procedure
Sodium benzenesulfinate (11.21 g, 68.27 mmol) was dissolved in water (100 ml). This solution was shaken with iodine (17.33 g, 68.27 mmol) in dichloromethane (100 ml). The dichloromethane layer turned from deep pink to orange. The dichloromethane layer was dried over magnesium sulphate and filtered into a flask containing methy 2-propylacrylate (5.0 g, 39.01 mmol). The solution was stired overnight at room temperature and then cooled to 0° C. Triethylamine (11 ml, 78.01 mmol) was added and the solution was allowed to warm to room temperature over 2 hours. The mixture was diluted with water and the organic layer was washed with 1N hydrochloric acid (75 ml), 10% aqueous sodium bisulfite (75 ml), and brine, then dried over magnesium sulfate, filtered and evaporated to give (E)-3-benzenesulfonyl-2-propylacrylic acid methyl ester (9.1 g, 87% yield).
Workup
- dry with materialThe dichloromethane layer was dried over magnesium sulphate
- filtrationfiltered into a flask
- temperatureto warm to room temperature over 2 hours
- washthe organic layer was washed with 1N hydrochloric acid (75 ml), 10% aqueous sodium bisulfite (75 ml), and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-67569568439841b3b1b4c793c333f6ab
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06274758B1
Reaction notes
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