Piperonal → 3,4-Ethylenedioxy-4'-[(3-tetrahydropyranyloxy)-1-propylsulfonyl]stilbene

HRID 440195Notes

Reaction equation

HRID 440195 reaction equation
CN(C)[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH2:20][CH2:21][CH2:22][O:23]C(C3CCCOC3)=O)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.CC1C=CC(S(CCCO[CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][O:48]2)(=O)=O)=CC=1.C1C(C=O)=C[C:56]2[O:61]C[O:63][C:55]=2C=1>ClCCl.C(OCC)(=O)C>[CH2:56]1[CH2:55][O:63][C:3]2[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]3[CH:12]=[CH:13][C:14]([S:17]([CH2:20][CH2:21][CH2:22][O:23][CH:50]4[CH2:51][CH2:52][CH2:47][O:48][CH2:49]4)(=[O:19])=[O:18])=[CH:15][CH:16]=3)=[CH:5][C:4]=2[O:61]1

Participants

5

Reactant 3

HCID 8438PiperonalHCID 220761783-(4-Methylphenyl)sulfonyl-1-tetrahydropyranyloxypropaneHCID 867494844-Dimethylamino-4'-[(3-tetrahydropyranoyloxy)-1-propylsulfonyl]stilbene

Product 1

HCID 545138473,4-Ethylenedioxy-4'-[(3-tetrahydropyranyloxy)-1-propylsulfonyl]stilbene

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

As in Example 3a 2.98 g (10 mmol) of 2a and 1.65 g (11 mol) of piperonal give, after column chromatography [silica gel; dichloromethane/ethyl acetate mixtures], 1.22 g (27%) of yellow oil.

Sources & evidence

ORD record
ord-152edae3a0d54323945db243092216fa
Source dataset
uspto-grants-1996_05
Patent number
US05517350

Reaction notes

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