Methanol → methyl 4-(2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate

Participants

Reaction Steps

4-Allyl-tetrahydro-pyran-4-carboxylic acid methyl ester (11 g, 59.78 mmol) was dissolved in iPrOH (300 mL). To this was added a aqueous solution of NaIO4 (28 g, 130.4 mmol, 2.18 equiv.) in water (300 mL), followed by addition of OsO4 (50 mg, crystals, in one portion) at rt. The solution was stirred with a mechanical stirrer at rt (water bath). After 30 min, milky cloudy mixture was formed. Stirring was continued for 4 h. TLC (1% MeOH in DCM, and 5% MeOH in DCM) did not detect the starting material. The reaction mixture was monitored by 1H NMR by taking an aliquot in CDCl3 periodically until no alkene peak was detected in the sample. At which time the reaction was judged to be complete. The reaction mixture was poured into ice water (200 mL) and EtOAc (200 mL). The two layers were separated and the aqueous layer was extracted with EtOAc (5×50 mL). More water was added to dissolve the solid to result a clear solution. The combined extracts were washed with brine, and concentrated to dryness to obtain the title compound as a crude liquid product. The product was subject to a distillation under reduced pressure to remove isopropanol. The residual product was then purified on a 80 g silica gel column, eluted with MeOH in DCM: 0% 0-5 min; 5-10% 5-25 min. 10-12% 25-60 min. Note: the product is not UV active. Anisaldehyde visualization was used. The product fractions were collected and concentrated to yield a liquid 6.6 g (60% yield) of the title compound.

Provenance & Evidence