Methyl iodide → (2R,5S)-2-(methoxymethyl)-5-vinyl-1,4-dioxane

To a solution of ((2R,5S)-5-vinyl-1,4-dioxan-2-yl)methanol (Preparation #17, 0.25 g, 1.734 mmol) in THF (3 mL) was added NaH (41.6 mg, 1.734 mmol) at 0° C. The reaction mixture was slowly warmed to RT and stirred for 25 min. The reaction mixture was cooled to about 0° C. and iodomethane (0.108 mL, 1.734 mmol) was added. Upon completion of addition, the reaction mixture was slowly warmed to RT and stirred for about 2.5 h. The reaction mixture was diluted with water (20 mL) and the product extracted with EtOAc (2×10 mL). The organic layer dried over sodium sulfate and concentrated under reduced pressure. The crude material obtained was purified by column chromatography eluting with 10% EtOAc in hexane to afford (2R,5S)-2-(methoxymethyl)-5-vinyl-1,4-dioxane 0.1 g (36.5%), 1H NMR (400 MHz, CDCl3): δ 5.75-5.67 (m, 1H), 5.36-5.32 (m, 1H), 5.23-5.20 (m, 1H), 4.05-4.00 (m, 1H), 3.87-3.70 (m, 3H), 3.55-3.49 (m, 1H), 3.42-3.35 (m, 6H), ES-MS: m/z 158 (m+H).

1. temperatureThe reaction mixture was cooled to about 0° C.
2. additionUpon completion of addition
3. temperaturethe reaction mixture was slowly warmed to RT
4. stirringstirred for about 2.5 h
5. extractionthe product extracted with EtOAc (2×10 mL)
6. dry with materialThe organic layer dried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe crude material obtained
9. customwas purified by column chromatography
10. washeluting with 10% EtOAc in hexane

ORD record

ord-b2eb76df2dcd4ede97bc582fe6e4ed10

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029409B2