9-ethyl-9H-carbazole-3-carbaldehyde → 1-(N-Ethylcarbazol-3-yl)-2-[4-(3-tetrahydropyranyloxy)-1-propylsulfonylphenyl]ethene

HRID 440194Notes

Reaction equation

HRID 440194 reaction equation
CN(C)C1C=CC(C=CC2[CH:16]=[CH:15][C:14]([S:17]([CH2:20][CH2:21][CH2:22]OC(C3CCCOC3)=O)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=CC=1.CC1C=CC(S(C[CH2:44][CH2:45][O:46][CH:47]2CCCCO2)(=O)=O)=CC=1.[CH2:53]([N:55]1[C:67]2[CH:66]=[CH:65][C:64](C=O)=[CH:63][C:62]=2[C:61]2[C:56]1=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH3:54].Cl[CH2:71]Cl.[C:73]([O:76][CH2:77][CH3:78])(=O)[CH3:74]>>[CH2:53]([N:55]1[C:67]2[CH:66]=[CH:65][C:64]([CH:16]=[CH:15][C:14]3([S:17]([CH2:20][CH2:21][CH3:22])(=[O:18])=[O:19])[CH:13]=[CH:12][C:73]([O:76][CH:77]4[CH2:78][CH2:44][CH2:45][O:46][CH2:47]4)=[CH:74][CH2:71]3)=[CH:63][C:62]=2[C:61]2[C:56]1=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH3:54]

Participants

5

Reactant 4

HCID 820559-ethyl-9H-carbazole-3-carbaldehydeHCID 21226138Dichloromethane ethylacetateHCID 220761783-(4-Methylphenyl)sulfonyl-1-tetrahydropyranyloxypropaneHCID 867494844-Dimethylamino-4'-[(3-tetrahydropyranoyloxy)-1-propylsulfonyl]stilbene

Product 1

HCID 677722001-(N-Ethylcarbazol-3-yl)-2-[4-(3-tetrahydropyranyloxy)-1-propylsulfonylphenyl]ethene

Procedure

As in Example 3a 2.98 g (10 mmol) of 2a and 2.68 g (12 mmol) of N-ethylcarbazole-3-carboxaldehyde give, after column chromatography. [silica gel; dichloromethane/ethyl acetate mixtures], 1.56 g (31%) of yellow oil.

Sources & evidence

ORD record
ord-a5e3cf8503d04f2b85406ce3dac2fac4
Source dataset
uspto-grants-1996_05
Patent number
US05517350

Reaction notes

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