9-ethyl-9H-carbazole-3-carbaldehyde → (E)-9-Ethyl-3-(4-(triphenylen-2-yl)styryl)-9H-carbazole

HRID 871821Notes

Reaction equation

[CH:1]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[C:19]1[CH:33]=[CH:32][C:22]([CH2:23]P(=O)(OCC)OCC)=[CH:21][CH:20]=1.[CH2:34]([N:36]1[C:48]2[CH:47]=[CH:46][C:45]([CH:49]=O)=[CH:44][C:43]=2[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH3:35].CC(C)([O-])C.[K+]>C1COCC1>[CH2:34]([N:36]1[C:48]2[CH:47]=[CH:46][C:45](/[CH:49]=[CH:23]/[C:22]3[CH:32]=[CH:33][C:19]([C:2]4[CH:3]=[CH:4][C:5]5[C:6]6[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=6)[C:12]6[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=6)[C:18]=5[CH:1]=4)=[CH:20][CH:21]=3)=[CH:44][C:43]=2[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH3:35]

Participants

Conditions

Temperature: 0 °C

Procedure

Compound E (100 mg, 0.22 mmol) or E1 and N-ethylcarbazole-3-carboxaldehyde) (59 mg, 0.26 mmol) and dry THF (10 ml) were charged in two-necked bottle in an ice bath, potassium-tert-butoxide (49 mg, 0.44 mmol) in dry THF (10 ml) was added under nitrogen. The reaction mixture was stirred for 15 min at 0° C., followed by 1 h at room temperature. The solution mixture was extracted with ethyl acetate and washed with water. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure to afford a crude product that was purified by sublimating at a temperature of 260° C. to obtain TSCz (90 mg, yield=78%) as yellow solid.

Workup

waitfollowed by 1 h at room temperature
extractionThe solution mixture was extracted with ethyl acetate
washwashed with water
dry with materialThe combined organic layers were dried over MgSO4
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-34003f5c160e48fc962726a91bea3525
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08974920B2

Reaction notes

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