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

HRID 1741972
Notes
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Reaction equation

HRID 1741972 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23665760Sodium HypochloriteHCID 867480474,5-(Dimethylmethylenedioxy)-3-(1-ethoxyethoxy)-6-heptenal oxime

Product 1

HCID 677934444,5-(Dimethylmethylenedioxy)-6-(1-ethoxyethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazoleYield 53.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl Ether
Solvent
HCID 6344DichloromethaneSolvent

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

  1. washwashed with a sodium hydrogen carbonate aqueous solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes