Water → Oxane-2-carboxylic acid

To a vigorously stirred solution of tetrahydropyran-2-methanol (2.32 g, 40 mmol) in a mixture of CH3CN (20 ml), CCl4 (20 ml) and water (10 ml) at 0° C. was added NaIO4 (9.42 g, 44 mmol) and then RuCl3H2O(414 mg, 2 mmol). After 20 min, the cooling bath was removed. After 40 min at room temperature, TLC showed reaction was complete. The reaction mixture was partitioned into ethyl acetate and ice-cold Na2S2O5 solution. More Na2S2O5 was added until all the brown material dissolved and a greenish mixture was obtained. The aqueous portion was extracted with more ethyl acetate and combined layer was washed with 10% Na2S2O5, H2O, brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using methylene chloride/methanol/acetic acid=95:5:0.5 to afford the product as an oil (1.5 g).

1. customthe cooling bath was removed
2. waitAfter 40 min at room temperature
3. customreaction
4. customThe reaction mixture was partitioned into ethyl acetate and ice-cold Na2S2O5 solution
5. additionMore Na2S2O5 was added until all the brown material
6. dissolutiondissolved
7. customa greenish mixture was obtained
8. extractionThe aqueous portion was extracted with more ethyl acetate
9. washwas washed with 10% Na2S2O5, H2O, brine
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated
13. customThe residue was purified by silica gel chromatography

ORD record

ord-af341403f2c640a4b77fe6304b473013

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06420418B1