Chloride → Isopropyl cyclopropanesulfonate

反応式

[CH3:1][CH:2]([OH:4])[CH3:3].[CH:5]1([S:8](Cl)(=[O:10])=[O:9])[CH2:7][CH2:6]1.[Cl-]>N1C=CC=CC=1>[CH:5]1([S:8]([O:4][CH:2]([CH3:3])[CH3:1])(=[O:10])=[O:9])[CH2:7][CH2:6]1

参加物

反応条件

温度: 0 °C

実験手順

IPA (11 L) was added to pyridine (1850 g; 1890 mL) at 20° C. with stirring for 1 hour. The solution was cooled to between −10° C. and 2° C. and cyclopropane sulfonic chloride (1100 g) was added dropwise followed by stirring at this temperature for 70 hours. NMR analysis showed 85% of sulfonic chloride was consumed in the reaction. The reaction was cooled to 0° C. and NaOH (312 g) in water (600 mL) was added dropwise. The resultant product was concentrated to dryness and 45° C. and diluted with EtOAc (2750 mL), MTBE (1375 mL). The solution was stirred for 10 minutes and filtered. Heptane (1375 mL) was added, filtered and the filtrate was concentrated to dryness giving 1080 g of product as a red liquid (84% yield). 1H NMR (CDCl3, 400 MHz): δ 4.86 (m, 1H), 2.83 (m, 1H), 1.33 (d, 6H), 0.98-1.10 (m, 4H).