Water → Methyl 4-methyloxane-4-carboxylate

Methyl tetrahydropyran-4-carboxylate (2.88 g, 20.0 mmol) was dissolved in THF (100 mL), and a 2.0 mol/L solution of lithium diisopropylamide in THF (22.0 ml, 44.0 mmol) was added thereto at 0° C., followed by stirring at room temperature for 30 minutes. Methyl iodide (4.98 ml, 40.0 mmol) was added dropwise to the reaction mixture, followed by stirring for 1 hour. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1) to afford methyl 4-methyltetrahydropyran-4-carboxylate (1.93 g, 61%).

1. customat 0° C.
2. stirringby stirring for 1 hour
3. extractionfollowed by extraction with ethyl acetate
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. distillationthe solvent was distilled away under reduced pressure
6. customthe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1)

ORD record

ord-ffeaec8650e84c0e9b09c411b4ac49bf

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889718B2