Water → 2,7-Bis(trimethylstannyl)-5,10-ditetradecyloxynaphtho[2,3-b:6,7-b']dithiophene

HRID 407201

Reaktionsgleichung

Reaktionsgleichung von HRID 407201
[CH2:1]([O:15][C:16]1[C:17]2[C:25]([CH:26]=[C:27]3[CH:31]=[CH:30][S:29][C:28]=13)=[C:24]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:20]1[S:21][CH:22]=[CH:23][C:19]=1[CH:18]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C([Li])CCC.[CH3:52][Sn:53](Cl)([CH3:55])[CH3:54].O>C1COCC1>[CH3:52][Sn:53]([CH3:55])([CH3:54])[C:22]1[S:21][C:20]2[C:24]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[C:25]3[C:17](=[CH:18][C:19]=2[CH:23]=1)[C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[C:28]1[S:29][C:30]([Sn:53]([CH3:55])([CH3:54])[CH3:52])=[CH:31][C:27]1=[CH:26]3

Komponenten

6

Edukt 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 708730165,10-Ditetradecyloxynaphtho[2,3-b:6,7-b']dithiopheneHCID 178418339Butyllithium

Produkt 1

HCID 866726382,7-Bis(trimethylstannyl)-5,10-ditetradecyloxynaphtho[2,3-b:6,7-b']dithiopheneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Compound (4b) (0.500 g, 0.752 mmol) was solubilized in anhydrous THF (40 mL) and cooled at −78° C. under N2. n-Butyllithium (0.75 mL, 2.5M) was then added and the stirring was continued for 30 minutes at this temperature and then 30 minutes at room temperature. The reaction mixture was cooled to −78° C. again before adding trimethylstannyl chloride (1.9 mL, 1.0M). The reaction was warmed up to room temperature and stirred overnight. The reaction was stopped by adding water, and the mixture was extracted with diethyl ether, dried over MgSO4, filtered, and concentrated in vacuo. The crude monomer was solubilized in 5 mL of THF and then dropped in methanol (200 mL). The product was allowed to precipitate in the freezer overnight before filtering and washing with cold methanol to afford a yellow fluffy powder as the title compound (0.650 g, 86%). 1H NMR (500 MHz, CDCl3, 298 K): 8.45 (s, 2H); 7.53 (s, 2H); 4.38 (t, J=6.6 Hz, 4H); 2.01 (quintet, J=7.9 Hz, 4H); 1.65 (quintet, J=7.7 Hz, 4H); 1.39 (m, 40H); 0.89 (t, J=7.0 Hz 6H); 0.47 (s, 18H) ppm. 13C NMR (125 MHz, CDCl3, 298 K): 149.07; 142.85; 141.22; 132.66; 130.48; 124.58; 109.85; 73.20; 31.96; 30.65; 29.76; 29.73; 29.70; 29.57; 29.41; 26.17; 22.73; 14.17; 8.38 ppm. HRMS (ESI-TOF-MS): m/z calcd for C48H80O2S2Sn2 990.3638, found 990.3670.

Aufarbeitung

  1. custom30 minutes
  2. customat room temperature
  3. temperatureThe reaction mixture was cooled to −78° C. again
  4. temperatureThe reaction was warmed up to room temperature
  5. extractionthe mixture was extracted with diethyl ether
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additiondropped in methanol (200 mL)
  10. customto precipitate in the freezer overnight
  11. filtrationbefore filtering
  12. washwashing with cold methanol

Quellen und Nachweise

ORD-Eintrag
ord-4825d6d5cd9d4b39ab0d92f1a15afa68
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754188B2

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