Triethylamine → 4-(2-Methanesulfonylethyl)-2,2-dimethyl-1,3-dioxolane

Temperature

-5 °C

4-(2-Hydroxylethyl)-2,2-dimethyl-1,3-dioxolane (25 g, 170 mmol), triethylamine (55.9 mL, 400 mmol), and a stir bar were added to a 1000 mL round bottom flask. The flask was sealed and flushed with nitrogen. Anhydrous DCM (600 mL) was added, and the mixture cooled to approx −5° C. (ice and NaCl). Mesyl chloride (19.9 mL, 255 mmol, 1.5 eq) was added slowly via syringe over a 60 minute period, and the reaction stirred at −5° C. for a further 1.5 hours. At this point TLC showed that the starting material had been consumed. The solution was diluted with DCM (350 mL), divided into two (˜500 mL) portions, and each portion worked up as follows: the solution was transferred to a 1000-mL separating funnel and washed with saturated NaHCO3 (2×200 mL). The organic phase was then dried (MgSO4), filtered, and concentrated (rotovap). The crude product was purified by column chromatography. Final yield: 32.0 g, 84.1%.

1. customThe flask was sealed
2. customflushed with nitrogen
3. additionAnhydrous DCM (600 mL) was added
4. customhad been consumed
5. additionThe solution was diluted with DCM (350 mL)
6. customseparating funnel
7. washwashed with saturated NaHCO3 (2×200 mL)
8. dry with materialThe organic phase was then dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated (rotovap)
11. customThe crude product was purified by column chromatography

ORD record

ord-91300f3c8ca34fcaa7b6b4f8761cebdd

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236943B2