反応 #9899

反応方程式

NBS

6-cyclobutyl-hexan-1-ol

triphenylphosphine

→

(6-bromo-hexyl)-cyclobutane

収率 91.3%

溶媒

DMF

反応条件

後処理

1. 1
   その他the reaction was quenched with methanol (0.5 mL)
2. 2
   workup.ADDITIONThe solution was diluted with ether (60 mL)
3. 3
   洗浄washed with water, saturated aqueous NaHCO3 and brine successively
4. 4
   その他The organic layer was dried
5. 5
   濃縮concentrated
6. 6
   その他The residue was purified by flash chromatography on silica gel
7. 7
   洗浄eluting with hexane

実験手順

To a solution of 6-cyclobutyl-hexan-1-ol (0.47 g, 3.0 mmol) in DMF (10 mL) was added triphenylphosphine (0.88 g, 3.4 mmol). The solution was cooled to 0° C. and NBS (0.57 g, 3.2 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.5 mL). The solution was diluted with ether (60 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford (6-bromo-hexyl)-cyclobutane (0.60 g, 91%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.40 (2H, t, J=6.9 Hz), 2.23 (1H, m), 2.02 (2H, m), 1.82 (4H, m), 1.55 (2H, m), 1.12–1.46 (8H, m); 13C NMR (75 MHz, CDCl3) δ 37.19, 36.39, 34.40, 33.11, 29.07, 28.68, 28.51, 27.26, 18.80.

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