HCID 23156925, Verbindung → HCID 117628943, Verbindung

HRID 57311

Reaktionsgleichung

Reaktionsgleichung von HRID 57311
[C:1]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2C(=O)[C:9]([C:26]3[CH:27]=[C:28]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:29]=[CH:30][CH:31]=3)=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH:2]=1.[CH2:45]([C:57]1[CH:62]=[CH:61][C:60]([C:63]#[C:64][C:65]2[CH:70]=[CH:69][C:68]([CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82])=[CH:67][CH:66]=2)=[CH:59][CH:58]=1)[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]>C1(OC2C=CC=CC=2)C=CC=CC=1.C1(=O)OC(C)CO1.CCCCCC>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[C:7]([C:3]3[CH:2]=[C:1]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH:6]=[CH:5][CH:4]=3)=[C:64]([C:65]3[CH:70]=[CH:69][C:68]([CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82])=[CH:67][CH:66]=3)[C:63]([C:60]3[CH:59]=[CH:58][C:57]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])=[CH:62][CH:61]=3)=[C:9]([C:26]3[CH:27]=[C:28]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:29]=[CH:30][CH:31]=3)[C:10]=2[C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[CH:13][CH:14]=1

Komponenten

6

Edukt 2

HCID 23156925HCID 23156925, VerbindungHCID 895341922,5-Di([1,1'-biphenyl]-3-yl)-3,4-bis(4-chlorophenyl)cyclopenta-2,4-dienone

Produkt 1

HCID 117628943HCID 117628943, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 7583Diphenyl EtherLösungsmittelHCID 7924Propylene CarbonateLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A degassed solution of 1.84 g of 2,5-di([1,1′-biphenyl]-3-yl)-3,4-bis(4-chlorophenyl)cyclopenta-2,4-dienone (8b, 3.03 mmol) and 1.72 g of 4,4′-didodecyltolane (3.34 mmol) in 12 ml of diphenyl ether and 5 ml of propylene carbonate was heated to 230° C. in a microwave reactor at power 300 watts and a maximum pressure of 7 bar for 2×12 h. After cooling to room temperature, the reaction solution was diluted with hexane and purified by column chromatography (silica, hexane with 6% ethyl acetate). After purification by means of recycling GPC and drying under high vacuum, 1.85 g of monomer 6b were obtained as a colorless oil (56%, 1.69 mmol). Elemental analysis measured: C 85.6; H 7.9% (calculated for C78H84Cl2: C, 85.8; H, 7.8%); 1H NMR (700 MHz, d8-THF) δ=7.27 (dt, J=7.7, 4.0 Hz, 4H, CH), 7.22-7.16 (m, 6H, CH), 7.10 (d, J=10.0 Hz, 4H, CH), 6.94 (t, J=7.7 Hz, 4H, CH), 6.91 (s, 2 Hv), 6.88 (d, J=8.4 Hz, 2H, CH), 6.87-6.81 (m, 2H, CH), 6.81-6.77 (m, 2H, CH), 6.77-6.70 (br m, 6H, CH), 6.66 (d, J=7.5 Hz, 2H, CH), 2.41-2.28 (m, 4H, α-CH2), 1.44-1.34 (m, 4H, β-CH2), 1.34-1.03 (m, 36H, —CH2—), 0.89 (t, J=6.9 Hz, 6H, —CH3); 13C NMR (175 MHz, d8-THF) δ=142.44, 142.42, 142.27, 141.88, 141.74, 140.76, 140.74, 140.68, 140.59, 140.56, 140.14, 140.10, 139.09, 139.05, 134.18, 134.14, 134.06, 134.01, 132.56, 132.50, 132.47, 132.30, 132.26, 131.69, 131.41, 129.37, 128.20, 128.07, 127.90, 127.88, 127.84, 127.81, 127.80, 127.74, 125.14, 125.12, 36.36, 36.33, 33.06, 32.37, 32.34, 30.85, 30.81, 30.77, 30.75, 30.61, 30.60, 30.51, 30.00, 29.98, 25.94, 25.82, 23.74, 14.62; MS (MALDI-TOF): m/z (%): 1091.0 (100) [M+] (calculated for C78H84Cl2: 1090.6); Rf (hexane with 6% ethyl acetate)=0.65.

Aufarbeitung

  1. customfor 2×12 h
  2. custompurified by column chromatography (silica, hexane with 6% ethyl acetate)
  3. customAfter purification by means of recycling GPC
  4. customdrying under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b486afc05ce44fe6b1fca30ea1b757b3
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434619B2

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