反応 #731295

反応方程式

1-chloro-6-iodohexane

thiophene

n-butyllithium

→

product

収率 92.0%

2-(6-Chlorohexyl)thiophene

収率 92.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.ADDITIONAfter complete addition
2. 2
   その他The reaction was quenched with sat. aq. ammonium chloride
3. 3
   抽出the reaction mixture was extracted with ethyl acetate (3×70 ml)
4. 4
   洗浄The combined organic extracts were washed with water, brine
5. 5
   乾燥dried over magnesium sulphate
6. 6
   その他The solvent was removed under reduced pressure

実験手順

To a stirred solution of thiophene (5.0 g, 59.5 mmol) in dry THF (50 ml) was added n-butyllithium (2.5 M in hexanes, 20.0 ml, 50.0 mmol) dropwise at −78° C. under nitrogen. After complete addition, the mixture was allowed to warm to room temperature, with stirring, over 2 h, followed by the addition of 1-chloro-6-iodohexane (12.3 g, 50.0 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with sat. aq. ammonium chloride, and the reaction mixture was extracted with ethyl acetate (3×70 ml). The combined organic extracts were washed with water, brine, and dried over magnesium sulphate. The solvent was removed under reduced pressure and the residue was chromatographyed (silica gel, petroleum ether), to afford the product as a pale yellow oil (9.3 g, 92%). 1H NMR (300 MHz, CDCl3): δ (ppm) 7.06 (dd, J=5.1 Hz, 1.2 Hz, 1H, Ar—H), 6.87 (dd, J=5.1 Hz, 3.4 Hz, 1H, Ar—H), 6.75 (m, 1H, Ar—H), 3.48 (t, J=6.6 Hz, 2H, ClCH2), 2.80 (t, J=7.4 Hz 2H, ArCH2), 1.61-1.78 (m, 4H, CH2), 1.29-1.50 (m, 4H, CH2); 13C NMR (75 MHz, CDCl3): δ (ppm) 145.5 (quat.), 126.7 (CH), 124.1 (CH), 122.9 (CH), 45.1 (CH2), 32.6 (CH2), 31.7 (CH2), 29.9 (CH2), 28.4 (CH2) 26.7 (CH2); MS (m/e) 204 (M+, 9%), 202 (M+, 3%), 97 (100).

出典