English to German Tech/Engineering Chemistry; Chem Sci/Eng

Aus einer Patentanmeldung für ein Diabetesmittel:

To a solution of the primary alcohol from example 1B (30.0 g, 64.2 mmol) in pyridine (67.5 mL) at -11[deg.] C. was added p-toluenesulfonyl chloride (15.57 g, 81.5 mmol) in pyridine (22.5 mL) dropwise over 35 minutes while maintaining the reaction temperature at -11 to -8[deg.] C. The reaction was mixed at -12[deg.] C. for an additional 6 hours then quenched by adding water (1.5 g). The quenched reaction mixture at -12.5[deg.] C. was added over a period of 5 minutes into a mixture of t-butyl methyl ether (180 mL) and 3N HCl (369 mL) and the layers were separated. The organic phase was washed with 7% NaHCO3 (90 mL), followed by 2% NaCl (90 mL), and finally with pH 7 buffer solution (90 mL). The organic phase was then concentrated under reduced pressure and ***chased*** with MTBE (90 mL), then acetone (90 mL) to afford 51.26 g of viscous oil. Acetone (386 mL) was added followed by sodium iodide (14.45 g, 96.4 mmol) and the reaction mixture was heated to reflux under nitrogen until the tosylate was consumed. MTBE (200 mL) and H2O (200 mL) were added to the cooled reaction mixture and the layers were separated. The organic phase was washed with H2O (150 mL), concentrated then chased with CH3CN. The product was isolated from CH3CN by filtration and dried to provide 29.51 g (76.9%) of the title compound.