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

HRID 1741972Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[O:19][CH:16]([CH:17]=[CH2:18])[CH:4]([CH:5]([O:10][CH:11]([O:13][CH2:14][CH3:15])[CH3:12])[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>[CH3:20][C:2]1([CH3:1])[O:3][CH:4]2[CH:5]([O:10][CH:11]([O:13][CH2:14][CH3:15])[CH3:12])[CH2:6][C:7]3[CH:17]([CH2:18][O:9][N:8]=3)[CH:16]2[O:19]1

Participants

Conditions

Temperature: 0 °C

Procedure

One gram of 4,5- (dimethylmethylenedioxy) -3-(1-ethoxyethoxy)-6-heptenal oxime was dissolved in 15 ml of methylene chloride, and 0.2 ml of triethylamine was added at 0° C. Then, 8 ml of a 10% sodium hypochlorite aqueous solution was added, and the mixture was stirred at 0° C. for 11 hours. The reaction mixture was diluted with ethyl ether, and washed with a sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution in sequence. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 530 mg of 4,5-(dimethylmethylenedioxy)-6-(1-ethoxyethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole having the following properties.

Workup

washwashed with a sodium hydrogen carbonate aqueous solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-95a8dba512eb490690c4c5aacbc73e61
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334740

Reaction notes

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