Water → 4,8-Dioctyl-2,6-bis-trimethylstannylbenzo[1,2-b:4,5-b']dithiophene

HRID 405042

반응식

HRID 405042 반응식
[CH2:1]([C:9]1[C:17]2[S:18][CH:19]=[CH:20][C:16]=2[C:15]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:11]2[S:12][CH:13]=[CH:14][C:10]=12)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([Li])CCC.[CH3:34][Sn:35](Cl)([CH3:37])[CH3:36].O>O1CCCC1>[CH2:1]([C:9]1[C:17]2[S:18][C:19]([Sn:35]([CH3:37])([CH3:36])[CH3:34])=[CH:20][C:16]=2[C:15]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:11]2[S:12][C:13]([Sn:35]([CH3:37])([CH3:36])[CH3:34])=[CH:14][C:10]=12)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

참가 물질

6

반응물 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 582808924,8-Dioctylbenzo[1,2-b:4,5-b']dithiopheneHCID 178418339Butyllithium

생성물 1

HCID 596091954,8-Dioctyl-2,6-bis-trimethylstannylbenzo[1,2-b:4,5-b']dithiophene수율 74%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4,8-dioctylbenzo[1,2-b:4,5-b′]dithiophene (782 mg, 1.89 mmol) in dry tetrahydrofuran (36 mL) was added n-butyllithium (2.5 M in hexane, 1.66 mL, 4.15 mmol) at −78° C. After 1 hour, trimethyltin chloride (877 mg, 4.40 mmol) was added in one portion. The mixture was stirred at room temperature for 2 hours, poured into water and extracted with ether three times. The organic layer was washed with brine and dried over anhydrous MgSO4. Upon evaporating the solvent, a pale yellow oil was obtained (1.03 g, yield 74%). Upon standing for one week, yellow crystals emerged and were collected (413 mg, yield 29%). 1H NMR (CDCl3, 500 MHz) δ=7.51 (s, 2H), 3.22 (t, J=8.0 Hz, 4H), 1.76-1.89 (m, 4H), 1.45-1.54 (m, 4H), 1.22-1.45 (bs, 16H), 0.90 (t, J=7.0 Hz, 6H), 0.47 (s, 18H).

후처리

  1. extractionextracted with ether three times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customUpon evaporating the solvent
  5. customa pale yellow oil was obtained (1.03 g, yield 74%)
  6. waitUpon standing for one week
  7. customwere collected (413 mg, yield 29%)

출처 및 근거

ORD 기록
ord-7a328ffc29174f4f9b05fa4d07f41849
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748739B2

연결된 노트

불러오는 중…