Methanol → Ethanesulfonyl fluoride, 2-(2-hydroxyethoxy)-

Into a round flask, HO(CH2)2OH (140.9 g) and a methanol solution of sodium methylate (28 wt %, 96.4 g) were charged and stirred, and heated under reduced pressure to distill off methanol thereby to obtain a solution of HOCH2CH2ONa. It was confirmed by GC that no methanol remained in the reaction solution. Into a four necked flask, FSO2CH2CH2Cl (50 g) and THF (100 mL) were charged and stirred under cooling with ice bath, and the previously obtained solution of HOCH2CH2ONa was dropwise added thereto over a period of 2.5 hours, while maintaining the internal temperature to be at most 10° C. After completion of the dropwise addition, it was stirred at room temperature for 2 hours and then added to water (400 mL), and dichloromethane (183 g) was added. The obtained crude liquid was subjected to liquid separation, and the obtained aqueous layer was extracted with dichloromethane (124 g). The separated aqueous layer was further extracted with dichloromethane (126 g), and the organic layers were put together. It was dried over magnesium sulfate, and after filtration, the solvent was distilled off to obtain a crude product (47.1 g). The obtained crude liquid was used for the next step without carrying out purification.

1. temperatureunder cooling with ice bath
2. temperaturewhile maintaining the internal temperature
3. customto be at most 10° C
4. additionAfter completion of the dropwise addition, it
5. stirringwas stirred at room temperature for 2 hours
6. additionwas added
7. customThe obtained crude liquid
8. customwas subjected to liquid separation
9. extractionthe obtained aqueous layer was extracted with dichloromethane (124 g)
10. extractionThe separated aqueous layer was further extracted with dichloromethane (126 g)
11. dry with materialIt was dried over magnesium sulfate
12. filtrationafter filtration
13. distillationthe solvent was distilled off

ORD record

ord-99d4e38a42464b0884c4213f78caf4b9

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06790982B2