Methoxymethyl-triphenylphosphonium chloride → 3-Methoxymethylene-8-oxa-bicyclo[3.2.1]octane

A solution of sodium bis(trimethylsilyl)amide 1M in THF (24.48 ml, 24.48 mmol) was added drop wise to a suspension of (methoxymethyl)triphenylphosphonium chloride (8.39 g, 24.48 mmol) in THF (98 ml) at −40° C. Stirring was continued for 0.5 h at −40° C. and then the solution of 8-oxa-bicyclo[3.2.1]octan-3-one [CAS #77745-32-5] (1.93 g, 15.3 mmol) in THF (20 ml) was added at −40° C. The suspension was allowed to warm to RT and stirring was continued for 6 h. The reaction mixture was quenched with a saturated solution of NH4Cl and extracted with EtOAc (2×). The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by silica gel column chromatography (eluting with a gradient of heptane-EtOAc 97:3 to 0:100) yielding the title compound as a slightly yellow oil (1.71 g, 11.09 mmol, 72%): 1H-NMR (400 MHz, CDCl3): δ 1.58-2.43 (m, 8H), 3.54 (s, 3H), 4.41 (m, 2H), 5.85 (s, 1H)

1. stirringstirring
2. waitwas continued for 6 h
3. customThe reaction mixture was quenched with a saturated solution of NH4Cl
4. extractionextracted with EtOAc (2×)
5. washThe combined organic phases were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated to dryness
9. customThe crude product was purified by silica gel column chromatography (
10. washeluting with a gradient of heptane-EtOAc 97:3 to 0:100)

ORD record

ord-e932610b970a416a8e051b87e25865e8

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859535B2