反応 #623920

反応方程式

cyclobutylmethanol

p-toluenesulfonyl chloride

→

title compound

収率 73.0%

cyclobutylmethyl 4-methylbenzenesulfonate

収率 73.0%

溶媒

CH2Cl2

pyridine

反応条件

後処理

1. 1
   その他then quenched with 5% aqueous HCl (30 mL)
2. 2
   その他The layers were separated
3. 3
   抽出the aqueous phase was extracted with CH2Cl2 (3×15 mL)
4. 4
   乾燥The combined organic extracts were dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他Purification by column chromatography (SiO2, 75% hexanes in EtOAc)

実験手順

To a solution of cyclobutylmethanol (25 g, 290 mmol) in CH2Cl2 (200 mL) and pyridine (100 mL) was added 4-(dimethylamino)pyridine (1.8 g, 14.5 mmol) followed by p-toluenesulfonyl chloride (55.3 g, 290 mmol). The mixture was allowed to stir at ambient temperature for 20 hours then quenched with 5% aqueous HCl (30 mL). The layers were separated and the aqueous phase was extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by column chromatography (SiO2, 75% hexanes in EtOAc) afforded the title compound (50.8 g, 211 mmol, 73% yield). MS (DCI/NH3) m/z 258 (M+NH4)+.

出典