Toluene → 5,10-Ditetradecyloxynaphtho[2,3-b:6,7-b']dithiophene

HRID 407199

反応式

HRID 407199 の反応式
[CH3:1][O:2][C:3]1[C:4]2[C:12]([CH:13]=[C:14]3[CH:18]=[CH:17][S:16][C:15]=13)=[C:11]([O:19][CH3:20])[C:7]1[S:8][CH:9]=[CH:10][C:6]=1[CH:5]=2.[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].[C:43]1(C)[CH:48]=[CH:47][C:46](S(O)(=O)=O)=[CH:45][CH:44]=1>O>[CH2:20]([O:19][C:11]1[C:12]2[C:4]([CH:5]=[C:6]3[CH:10]=[CH:9][S:8][C:7]=13)=[C:3]([O:2][CH2:1][CH2:47][CH2:48][CH2:43][CH2:44][CH2:45][CH2:46][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:21][CH3:27])[C:15]1[S:16][CH:17]=[CH:18][C:14]=1[CH:13]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH3:29]

参加物

6

反応物 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 82091-TetradecanolHCID 683593795,10-Dimethoxynaphtho[2,3-b:6,7-b']dithiophene

生成物 1

HCID 708730165,10-Ditetradecyloxynaphtho[2,3-b:6,7-b']dithiophene収率 49%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  1. customfitted with a condenser
  2. customwas placed in a 130° C.
  3. temperatureheat bath
  4. extractionextracted with dichloromethane
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified via column chromatography (20% dichloromethane in hexanes)

出典と根拠

ORDレコード
ord-0f0787b308ab49ea9e202ecd078b3a47
出典データセット
uspto-grants-2014_06
特許番号
US08754188B2

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