Methyl iodide → HCID 178496638, Verbindung

To a solution of cis-3-benzyloxymethylcyclobutanol (Albany Molecular Research Institute, 1.0 g, 5.2 mmol) in 10 mL of tetrahydrofuran at 0° C. was added NaH (0.62 g, 15.6 mmol). The mixture stirred for 15 minutes and iodomethane (0.49 mL, 7.8 mmol) was added and the mixture was allowed to warm to ambient temperature and stirred for 16 hours. Some starting material remained by TLC so additional NaH (0.21, 5.2 mmol) and iodomethane (0.32 mL, 5.2 mmol) were added and the mixture stirred for an additional 2 hours. The mixture was quenched with 10 mL of NH4Cl and diluted with 10 mL of ethyl acetate. The layers were separated and the aqueous layer was extracted twice with 5 mL portions of ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 75% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 207 (M+H)+.

1. stirringstirred for 16 hours
2. additionwere added
3. stirringthe mixture stirred for an additional 2 hours
4. customThe mixture was quenched with 10 mL of NH4Cl
5. additiondiluted with 10 mL of ethyl acetate
6. customThe layers were separated
7. extractionthe aqueous layer was extracted twice with 5 mL portions of ethyl acetate
8. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customPurification via column chromatography (SiO2, 75% hexanes in ethyl acetate)

ORD-Eintrag

ord-a4871e9d8c1b44219fbc9f8affc1cd94

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08841334B2