9-ethyl-9H-carbazole-3-carbaldehyde → 3-(2,2-Diphenylethenyl)-9-ethyl-9H-carbazole

HRID 1597725Notes

Reaction equation

HRID 1597725 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH2:16][CH3:17])[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3)=O.[C:18]1([CH:24](P([O-])(OCC)OCC)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC(C)([O-])C.[K+]>CN(C=O)C>[C:18]1([C:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:1][C:3]2[CH:4]=[CH:5][C:6]3[N:7]([CH2:16][CH3:17])[C:8]4[C:13]([C:14]=3[CH:15]=2)=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 820559-ethyl-9H-carbazole-3-carbaldehydeHCID 23665647Potassium tert-butoxideHCID 178476835HCID 178476835, compound

Product 1

HCID 145496403-(2,2-Diphenylethenyl)-9-ethyl-9H-carbazoleYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25.3 g (111.7 mmol) of 3-formyl-9-ethylcarbazole (2') (manufactured by Tokyo Kasei Kogyo Co.), 39.6 g (122.9 mmol) of diethyl diphenylmethylphosphite, 253 ml of DMF and 15.04 g (134.0 mmol) of potassium-t-butoxide were allowed to react and after treated in the same manner as with Example 1 (2) to obtain 36.44 g of 3-(2',2'-diphenylvinyl)-9-ethylcarbazole.

Workup

  1. customto react

Sources & evidence

ORD record
ord-812098ed2e2d4a8a8ca6e7f0b636184a
Source dataset
uspto-grants-1998_04
Patent number
US05736284

Reaction notes

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