Methoxymethyl-triphenylphosphonium chloride → Methoxyvinyl Sulfoxide

Temperature

-78 °C

To a suspension of methoxymethyl triphenylphosphonium chloride (1.42 g, 4.14 mmol) in dry THF (15 mL) at -78° C. was added dropwise a 1.77M phenyllithium solution (2.34 mL, 4.14 mmol), and the cooling bath was removed. Stirring was continued for 3 h to give a deep red solution. This solution was cooled to -78° C., and a solution of keto phenyl sulfoxide 110 in THF (10 mL) was added dropwise by cannula. The resulting mixture was then allowed to warm to rt over 5 h, stirred for an additional 5 h, and quenched with water (25 mL). The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated to give the crude product. Purification by silica gel chromatography (1:1=hexane:ethyl acetate) afforded 0.644 g (89%) of the desired product 111 as a mixture of the four diasteromers. 1H NMR (400 MHz, CDCl3); δ 1.20-2.98 (m, 13H), 3.47, 3.49, 3.52, 3.53 (s, 3H), 5.69, 5.71, 5.80, and 5.81 (br s, 1H), 7.22-7.66 (m, 5H).

1. customthe cooling bath was removed
2. customto give a deep red solution
3. temperatureto warm to rt over 5 h
4. stirringstirred for an additional 5 h
5. customquenched with water (25 mL)
6. extractionThe mixture was extracted with ethyl acetate
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated
9. customto give the crude product
10. customPurification by silica gel chromatography (1:1=hexane:ethyl acetate)

ORD record

ord-9f63c1d97e3b48c99062d365850edf69

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05932591