Methyl (R)-(-)-3-benzyloxy-2-methyl propanoate (CAS NO.: ) could be produced through the following synthetic routes.
 

A. 2-Benzyloxypyridine (CAS NO.: ). A 500-mL, three-necked, round-bottomed flask equipped with a magnetic stir bar, a thermocouple probe, a glass stopper, and a Dean-Stark trap with reflux condenser and a nitrogen bubbler is charged with benzyl alcohol (11.7 g, 0.108 mol, 1.0 equiv), 2-chloropyridine (13.5 g, 0.119 mol, 1.1 equiv), potassium hydroxide (20.0 g, 0.356 mol, 3.3 equiv), and toluene (210 mL) by temporary removal of the glass stopper. The suspension is stirred and (1.43 g, 5.40 mmol, 0.05 equiv) is added in one portion. The reaction mixture is heated to reflux with azeotropic removal of for 1 h. The reaction mixture is then allowed to cool to 25 °C. The fittings of the flask are removed. Water (100 mL) is added to the cooled reaction mixture and the resulting biphasic solution is transferred to a 500-mL separatory funnel. The reaction flask is rinsed with 50 mL of toluene and the rinse is combined with the reaction mixture. The lower, strongly basic aqueous layer (pH 14) is removed. The organic phase is washed a second time with water (100 mL) and the aqueous layer (pH 7) is removed. The cloudy, colorless organic phase is transferred to a 500-mL flask and concentrated under reduced pressure on a rotary evaporator (25–45 mmHg, bath temperature 45–50 °C). Residual water remaining in the organic phase is azeotropically removed during the concentration, to provide the crude product as a clear and colorless to pale yellow oil. This material is transferred to a 100-mL single-necked round-bottomed flask with magnetic stir bar and purified by vacuum distillation using a short-path distillation apparatus. A single fraction is collected (bp 93–95 °C, 1.0 mmHg) providing 19.0–19.2 g (95–96%) of 2-benzyloxypyridine as a colorless liquid.

B. 2-Benzyloxy-1-methylpyridinium trifluoromethanesulfonate (CAS NO.: ). A three-necked, 250-mL, round-bottomed flask equipped with a nitrogen bubbler inlet, thermocouple probe, rubber septum and overhead mechanical stirrer is charged with 2-benzyloxypyridine (10.6 g, 57.3 mmol, 1.0 equiv) and toluene (60 mL) by temporary removal of the septum. The resulting solution is cooled to 0 °C in an ice bath. (6.80 mL, 60.1 mmol, 1.05 equiv) is added dropwise via syringe over 15 min, during which time white solids crystallize and the internal temperature increases to approximately 15 °C. The ice bath is removed and the viscous slurry is allowed to warm to ambient temperature. After 1 h, the heterogeneous reaction mixture is diluted with 50 mL of hexanes and the solids are isolated by filtration and washed with one additional portion of hexanes (50 mL). After drying under vacuum, 19.6–19.8 g (98.5–99%) of 2-benzyloxy-1-methylpyridinium trifluoromethanesulfonate is isolated as a white, microcrystalline solid.

C. Methyl (R)-(-)-3-benzyloxy-2-methyl propanoate (CAS NO.: ). An oven-dried, 250-mL, three-necked, round-bottomed flask is equipped with a reflux condenser with an inert gas bubbler, a magnetic stir bar, a thermocouple probe and a glass stopper. 2-Benzyloxy-1-methylpyridinium trifluoromethanesulfonate (16.7 g, 48.0 mmol, 2.0 equiv), magnesium oxide (1.94 g, 48.0 mmol, 2.0 equiv), α,α,α-trifluorotoluene (48 mL) and methyl (R)-(-)-3-hydroxy-2-methyl propionate (2.65 mL, 23.8 mmol, 1.0 equiv) are charged to the reaction flask by temporarily removing the glass stopper. The heterogeneous reaction mixture is then heated in an oil bath (83 °C bath temperature, 80–82 °C internal temperature) for 24 h. The reaction mixture is allowed to cool to room temperature and suction filtered through a pad of Celite on a sintered glass funnel. The Celite is washed with methylene chloride (2 × 20 mL). The filtrate is concentrated by rotary evaporation (15 mmHg, 25 °C bath temperature), and the light brown oil is purified by flash column chromatography to provide 3.77–4.10 g (76–82%) of methyl (R)-(-)-3-benzyloxy-2-methyl propanoate as a colorless liquid.

Notice: Exercise care in the handling of 18-Crown-6 (harmful, target organ: nerves) and methyl triflate (corrosive, causes burns, target organs: eyes, skin, mucous membranes).