Hydrochloric Acid → 2-Methylene-3,4-(dimethylmethylenedioxy)-5-(methoxymethoxy)cyclohexanone
Reaction equation
O[CH2:2][CH:3]1[CH:8]2[O:9][C:10]([CH3:13])([CH3:12])[O:11][CH:7]2[CH:6]([O:14][CH2:15][O:16][CH3:17])[CH2:5][C:4]1=[O:18].CS(Cl)(=O)=O.Cl>N1C=CC=CC=1>[CH2:2]=[C:3]1[CH:8]2[O:9][C:10]([CH3:13])([CH3:12])[O:11][CH:7]2[CH:6]([O:14][CH2:15][O:16][CH3:17])[CH2:5][C:4]1=[O:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Pyridine (0.5 ml) was added to 22 mg of 2-hydroxymethyl-3,4-(dimethylmethylenedioxy)-5-(methoxymethoxy)cyclohexanone, and 0.1 ml of methanesulfonyl chloride was then added at 0° C., followed by stirring the mixture for 2 hours. The reaction mixture was poured into cold dilute hydrochloric acid, and extracted with diethyl ether. The extract was washed with a saturated sodium hydrogen carbonate aqueous solution and then with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to provide 1.8 mg of 2-methylene-3,4-(dimethylmethylenedioxy)-5-(methoxymethoxy)cyclohexanone having the following properties (yield 8.8%).
Workup
- additionwas then added at 0° C.
- extractionextracted with diethyl ether
- washThe extract was washed with a saturated sodium hydrogen carbonate aqueous solution
- dry with materialwith a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-552880e9b5034f1990fb48fe014ef201
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05334740
Reaction notes
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