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Water → 4,8-Bis(2-ethylhexyl)-2,6-bis-trimethlstannylbenzo[1,2-b:4,5-b']dithiophene

HRID 405044
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HRID 405044 반응식
[CH2:1]([CH:3]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:4][C:5]1[C:13]2[S:14][CH:15]=[CH:16][C:12]=2[C:11]([CH2:17][CH:18]([CH2:23][CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22])=[C:7]2[S:8][CH:9]=[CH:10][C:6]=12)[CH3:2].C([Li])CCC.[CH3:34][Sn:35](Cl)([CH3:37])[CH3:36].O>O1CCCC1>[CH2:23]([CH:18]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:17][C:11]1[C:7]2[S:8][C:9]([Sn:35]([CH3:37])([CH3:36])[CH3:34])=[CH:10][C:6]=2[C:5]([CH2:4][CH:3]([CH2:1][CH3:2])[CH2:25][CH2:26][CH2:27][CH3:28])=[C:13]2[S:14][C:15]([Sn:35]([CH3:37])([CH3:36])[CH3:34])=[CH:16][C:12]=12)[CH3:24]
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참가 물질

6

반응물 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 596092024,8-Bis(2-ethylhexyl)benzo[1,2-b:4,5-b']dithiopheneHCID 178418339Butyllithium

생성물 1

HCID 584349014,8-Bis(2-ethylhexyl)-2,6-bis-trimethlstannylbenzo[1,2-b:4,5-b']dithiophene수율 100%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of 4,8-bis(2-ethylhexyl)benzo[1,2-b:4,5-b′]dithiophene (237 mg, 0.57 mmol) in dry tetrahydrofuran (11 mL) was added n-butyllithium (2.5 M in hexane, 0.5 mL, 1.25 mmol) at −78° C. After 1 hour, trimethyltin chloride (264 mg, 1.32 mmol) was added in one portion. The mixture was stirred at room temperature for 2 hours, poured into water (20 mL) 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 (437 mg, yield 100%). Upon standing in a freezer for 2 days, pale yellow crystals emerged and were collected (326 mg, yield 77%). 1H NMR (CDCl3, 500 MHz) δ=7.51 (s, 2H), 3.07-3.23 (m, 4H), 1.96-2.07 (m, 2H), 1.21-1.50 (m, 16H), 0.94 (t, J=7.0 Hz, 6H), 0.89 (t, J=7.0 Hz, 6H), 0.46 (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 (437 mg, yield 100%)
  6. waitUpon standing in a freezer for 2 days
  7. customwere collected (326 mg, yield 77%)

출처 및 근거

ORD 기록
ord-593c97c5b396440e84fc80988bb8328a
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748739B2

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