反応 #1838501

反応方程式

tributylstannyl chloride

EDOT

THF

LDA

→

oil 6

収率 92.0%

2,5-bis(tributylstannyl)-3,4-ethylenedioxythiophene

収率 92.0%

溶媒

water ethylacetate

反応条件

後処理

1. 1
   温度cooled to 0
2. 2
   workup.ADDITIONafter addition
3. 3
   workup.ADDITIONwas added
4. 4
   workup.STIRRINGby stirring at 0 for 1 hour
5. 5
   その他An organic layer was separated from the reactant
6. 6
   洗浄the separated organic layer was washed with water
7. 7
   乾燥lastly dried with anhydrous sodium sulfate
8. 8
   その他The solvent was evaporated under reduced pressure
9. 9
   その他thus-obtained residues
10. 10
    その他were purified by flash chromatography
11. 11
    workup.ADDITIONpre-treated with triethylamine

実験手順

EDOT (5, 1.42 g, 10 mmol) was dissolved into anhydrous THF (40 ml) and cooled to 0. After stirring at 0 for 15 minutes, LDA (15 mL, 2M, THF/heptane/ethylebenzene) was added for 15 minutes, and after addition was complete, a reaction mixture was heated to room temperature for 1 hour. The reaction mixture was cooled to 0 and tributylstannyl chloride (8.1 ml, 30 mmol) was added thereto, followed by stirring at 0 for 1 hour, and water ethylacetate were added thereto. An organic layer was separated from the reactant and the separated organic layer was washed with water and lastly dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and thus-obtained residues were purified by flash chromatography using hexane as eluent in silica gel pre-treated with triethylamine to obtain a colorless oil 6 (6.61 g, 92%). 1H NMR (CDCl3, 400 MHz, d/ppm): 4.03-4.02 (d, J=4 Hz, 4H2OCH2CH2O), 1.60-1.40 (m, 12, 2×Sn—(CH2—)3), 1.26-1.20 (m, 12H, 2×Sn—(CH2CH2—)3), 1.00 (m, 12H, 2×Sn—(CH2CH2CH2—)3), 0.83-0.79 (m, 18H, 2×(CH3)3). 13C NMR (CDCl3, 100 MHz, d/ppm): 148.29, 115.81, 64.62, 29.01, 27.20, 13.69, 10.48. C30H58O2SSn2 (720.27): Theoretical value C, 50.03; H, 8.12; S, 4.45; Sn, 32.96; Experimental value C, 50.18; H, 8.08; S, 4.39.

出典