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

HRID 592503

Reaktionsgleichung

Reaktionsgleichung von HRID 592503
[CH2:1]([CH:9]([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH2:10][O:11][C:12]1[C:13]2[C:21]([CH:22]=[C:23]3[CH:27]=[CH:26][S:25][C:24]=13)=[C:20]([O:28][CH2:29][CH:30]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:16]1[S:17][CH:18]=[CH:19][C:15]=1[CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([Li])CCC.[CH3:64][Sn:65](Cl)([CH3:67])[CH3:66].O>C1COCC1>[CH3:64][Sn:65]([CH3:67])([CH3:66])[C:26]1[S:25][C:24]2[C:12]([O:11][CH2:10][CH:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])=[C:13]3[C:21](=[CH:22][C:23]=2[CH:27]=1)[C:20]([O:28][CH2:29][CH:30]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[C:16]1[S:17][C:18]([Sn:65]([CH3:67])([CH3:66])[CH3:64])=[CH:19][C:15]1=[CH:14]3

Komponenten

6

Edukt 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 708730075,10-Bis(2-octyldodecyloxy)naphtho[2,3-b:6,7-b']dithiopheneHCID 178418339Butyllithium

Produkt 1

HCID 890521032,7-Bis(trimethylstannyl)-5,10-bis(2-octyldodecyloxy)naphtho[2,3-b:6,7-b']dithiopheneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Compound (4a) (0.350 g, 0.420 mmol) was solubilized in anhydrous THF (17 mL) and cooled at −78° C. under N2. n-Butyllithium (0.42 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 (1.1 mL, 1.0 M). 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 (0.420 g, 86%). 1H NMR (500 MHz, CDCl3, 298 K): 8.43 (s, 2H); 7.51 (s, 2H); 4.29 (d, J=5.4 Hz, 4H); 2.00 (quintet, J=6.0 Hz, 2H); 1.74 (m, 4H); 1.45 (m, 60H); 0.88 (m, 12H); 0.47 (s, 18H) ppm. 13C NMR (125 MHz, CDCl3, 298 K): 149.22; 142.73; 141.25; 132.62; 130.19; 124.51; 109.71; 75.50; 39.37; 31.99; 31.97; 31.42; 30.23; 29.83; 29.82; 29.78; 29.75; 29.47; 29.42; 27.08; 22.74; 14.19; 14.18; 8.40 ppm. HRMS (ESI-TOF-MS): m/z calcd for C60H104O2S2Sn2 1158.5516. found 1158.5543.

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-dcd8c3f28b3441ebbb0fa5cc61ef006c
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09240556B2

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