Ethanol → Sodium 4-chloromethyl-7-hydroxy-8-methylcoumarin-4-methanesulfonate
Reaction equation
[Cl:1][CH2:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:14])[C:9]([OH:13])=[CH:10][CH:11]=2)[O:6][C:5](=[O:15])[CH:4]=1.[S:16]([O-:19])([O-:18])=[O:17].[Na+:20].[Na+].[CH2:22](O)C>O>[Cl:1][CH2:2][C:3]1([CH2:22][S:16]([O-:19])(=[O:18])=[O:17])[C:12]2[C:7](=[C:8]([CH3:14])[C:9]([OH:13])=[CH:10][CH:11]=2)[O:6][C:5](=[O:15])[CH2:4]1.[Na+:20]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1 g of the compound 5 dissolved in 90 mL of ethanol is introduced into a flask, and then a solution of sodium sulfite (1.1 equivalents, 617 mg) in 22 mL of water is added. The mixture is refluxed. After 20 hours of heating, the mixture is cooled to 0° C. The solution is filtered on a Büchner funnel, the obtained beige residue is washed with ethanol, as for the filtrate, it is evaporated under reduced pressure in order to obtain a yellow solid. This solid is washed with ethanol and diethyl ether. Both obtained solids are collected in order to obtain 1 g (80%) of the crude compound 6.
Workup
- additionis introduced into a flask
- temperatureThe mixture is refluxed
- temperatureAfter 20 hours of heating
- filtrationThe solution is filtered on a Büchner funnel
- washthe obtained beige residue is washed with ethanol, as for the filtrate, it
- customis evaporated under reduced pressure in order
- customto obtain a yellow solid
- washThis solid is washed with ethanol and diethyl ether
- customBoth obtained solids are collected in order
Sources & evidence
- ORD record
- ord-907e5cf50bbc4ab8a37aa453eeef811d
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716496B2
Reaction notes
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