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

HRID 592504

반응식

HRID 592504 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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, 1.0 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 (0.650 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.

후처리

  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

출처 및 근거

ORD 기록
ord-17de24ea63ca49bc9bdd11ee06a9b9f1
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09240556B2

연결된 노트

불러오는 중…