Pyridine → 4-Hydroxy-5-methoxycarbonyloxy-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole
Reaction equation
[OH:1][CH:2]1[CH:7]2[CH2:8][O:9][N:10]=[C:6]2[CH2:5][CH:4]([O:11][CH2:12][O:13][CH3:14])[CH:3]1[OH:15].N1C=CC=CC=1.[C:22](Cl)(=[O:25])[O:23][CH3:24]>C(Cl)Cl.C(OCC)C>[OH:1][CH:2]1[CH:7]2[CH2:8][O:9][N:10]=[C:6]2[CH2:5][CH:4]([O:11][CH2:12][O:13][CH3:14])[CH:3]1[O:15][C:22]([O:23][CH3:24])=[O:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
4,5-Dihydroxy-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole (217 mg) was dissolved in 10 ml of methylene chloride, and 1 ml of pyridine and then 100 mg of methyl chlorocarbonate were added under ice cooling. The mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with diethyl ether, washed with dilute hydrochloric acid, a sodium hydrogen carbonate aqueous solution and a sodium chloride aqueous solution in sequence. The organic layer was dried over anhydrous sodium sulfate, and concentrated was under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 137 mg of 4-hydroxy-5-methoxycarbonyloxy-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole having the following property (yield 50%).
Workup
- washwashed with dilute hydrochloric acid
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-3fbb531900484276a227dc177a666478
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05334740
Reaction notes
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