Reaktion #474059

Reaktionsgleichung

2-[(3S)-oxolan-3-yl]ethan-1-ol

triethyl amine

methanesulfonyl chloride

→

2-[(3R)-oxolan-3-yl]ethyl methanesulfonate

Ausbeute 100.0%

Lösungsmittel

THF

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with saturated aqueous NaHCO3 solution (2×5 mL) and 1M aqueous HCl solution (2×5 mL)
2. 2
   TrocknenThe organic layer is dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenthe filtrate is concentrated under reduced pressure

Vorschrift

To a solution of 1.00 g (0.861 mmol) of 2-[(3S)-oxolan-3-yl]ethan-1-ol in anhydrous THF (1.5 mL) are added triethyl amine (0.13 mL, 0.947 mmol) and methanesulfonyl chloride (0.07 mL, 0.947 mmol) slowly at 0° C. The reaction is stirred at room temperature for 2 h. The mixture is diluted with ethyl acetate (20 mL) and washed with saturated aqueous NaHCO3 solution (2×5 mL) and 1M aqueous HCl solution (2×5 mL). The organic layer is dried (MgSO4), filtered and the filtrate is concentrated under reduced pressure to afford 167 mg of 2-[(3R)-oxolan-3-yl]ethyl methanesulfonate. Yield: 100%, 1H NMR (250 MHz, CHLOROFORM-d) δ ppm 1.40-1.60 (1H, m), 1.70-1.87 (1H, m), 1.95-2.12 (1H, m), 2.16-2.37 (1H, m), 2.96 (3H, s), 3.32 (1H, dd, J=8.22, 7.16 Hz), 3.62-3.91 (3H, m), 4.13-4.24 (2H, m).

Quelle