تفاعل #679684

معادلة التفاعل

Compound ( 3 )

5,10-Dimethoxynaphtho[2,3-b:6,7-b′]dithiophene

Toluene

1-tetradecanol

p-toluenesulfonic acid

→

compound ( 4b )

المردود 49.0%

5,10-Ditetradecyloxynaphtho[2,3-b:6,7-b′]dithiophene

المردود 49.0%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   أخرىfitted with a condenser
2. 2
   أخرىwas placed in a 130° C.
3. 3
   درجة الحرارةheat bath
4. 4
   استخلاصextracted with dichloromethane
5. 5
   تجفيفdried over MgSO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىThe product was purified via column chromatography (20% dichloromethane in hexanes)

الإجراء التجريبي

Compound (3) (0.500 g, 1.66 mmol) was weighed into a flame-dried 2-neck flask fitted with a condenser. Toluene (17 mL), 1-tetradecanol (1.42 g, 6.64 mmol), and p-toluenesulfonic acid (0.063 g, 0.332 mmol) were then added. The mixture was placed in a 130° C. heat bath and stirred overnight. The mixture was diluted with water, extracted with dichloromethane, dried over MgSO4, filtered, and concentrated. The product was purified via column chromatography (20% dichloromethane in hexanes) to yield compound (4b) as a yellow solid (0.540 g, 49%). 1H NMR (500 MHz, CDCl3, 298 K): 8.48 (s, 2H); 7.47 (m, 4H); 4.38 (t, J=6.6 Hz, 4H); 2.02 (quintet, J=7.7 Hz, 4H); 1.65 (quintet, J=7.8 Hz, 4H); 1.39 (m, 40H); 0.89 (t, J=7.1 Hz 6H) ppm. 13C NMR (125 MHz, CDCl3, 298 K): 149.74; 139.68; 128.05; 127.36; 124.87; 124.64; 110.97; 73.54; 31.96; 30.66; 29.73; 29.70; 29.54; 29.40; 26.18; 22.73; 14.17 ppm. HRMS (ESI-TOF-MS): m/z calcd for C42H64O2S2 664.4348. found 664.4356.

المصدر