2,6-Lutidine → HCID 70981364, compound

Temperature

-78 °C

6-Hydroxy-2H-pyran-3(6H)-one (9 g, 79 mmol) was dissolved in DCM (250 mL), placed under a nitrogen atmosphere, and cooled to −78° C. 2,6-Lutidine (13.78 mL, 118 mmol) was then added in one portion, followed by slow addition of t-butyldimethylsilyltrifluoromethanesulfonate (21.74 mL, 95 mmol). The reaction was allowed to slowly warm to 0° C. over 4 h. The reaction was quenched by addition of ˜20 mL of water. The solution turned pale yellow upon quenching. After transferring to a separatory funnel, the organic phase was washed successively with 10% citric acid and brine. The organic layer was then dried over sodium sulfate, filtered and condensed to give a yellow oil. The crude material was purified on a 340G SNAP Biotage column (0-20% ethyl acetate in hexane) to give 6-(tert-butyldimethylsilyloxy)-2H-pyran-3(6H)-one (9.90 g, 43.4 mmol, 55.0% yield) as a yellow oil; 1H NMR (400 MHz, CDCl3) δ ppm 6.87 (dd, J=10.54, 3.12 Hz, 1H), 6.08 (d. J=10.15 Hz, 1H), 5.53 (d, J=3.12 Hz, 1H), 4.51 (d, J=16.79 Hz, 1H), 4.08 (d, J=16.79 Hz, 1H), 0.92 (s, 9H), 0.17 (s, 6H).

1. temperatureto slowly warm to 0° C. over 4 h
2. customThe reaction was quenched by addition of ˜20 mL of water
3. customupon quenching
4. customAfter transferring to a separatory funnel
5. washthe organic phase was washed successively with 10% citric acid and brine
6. dry with materialThe organic layer was then dried over sodium sulfate
7. filtrationfiltered
8. customcondensed
9. customto give a yellow oil
10. customThe crude material was purified on a 340G SNAP Biotage column (0-20% ethyl acetate in hexane)

ORD record

ord-5bcd7efb7b304cb1bf1a3395d5bd98da

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139534B2