Triethylamine → 4,5-(Dimethylmethylenedioxy)-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole

HRID 1741959Notes

Reaction equation

[CH3:1][C:2]1([CH3:18])[O:17][CH:14]([CH:15]=[CH2:16])[CH:4]([CH:5]([O:10][CH2:11][O:12][CH3:13])[CH2:6][CH:7]=[N:8][OH:9])[O:3]1.C(N(CC)CC)C.Cl[O-].[Na+]>C(Cl)Cl.C(OCC)C>[CH3:1][C:2]1([CH3:18])[O:3][CH:4]2[CH:5]([O:10][CH2:11][O:12][CH3:13])[CH2:6][C:7]3[CH:15]([CH2:16][O:9][N:8]=3)[CH:14]2[O:17]1

Participants

Conditions

Temperature: 0 °C

Procedure

4,5-(Dimethylmethylenedioxy)-3-methoxymethoxy-6-heptenal oxime (89.5 mg) was dissolved in 4 ml of methylene chloride, and 0.035 ml of triethylamine was added at 0° C. A 10 % sodium hypochlorite aqueous solution (2.6 ml) was added at 0° C., and the mixture was stirred at 0° C. for 57 hours. The reaction mixture was diluted with diethyl ether, and washed with saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution in sequence. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography to provide 0.0 mg of 4,5-(dimethylmethylenedioxy)-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole having the following properties (yield 56%).

Workup

washwashed with saturated sodium hydrogen carbonate aqueous solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
custompurified by silica gel column chromatography

Sources & evidence

ORD record: ord-3d914b5c23694b5286abb1c4b9f67a8e
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334740

Reaction notes

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