Dimethyl Sulfide → (R,E)-4-phenylthio-3-buten-2-ol

(E)-4-phenylthio-3-buten-2-one (178 mg, 1.0 mmol), (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c] [1,3,2] oxazaborol (28 mg, 0.1 mmol) and MS4A (Nacalai Tesque Inc., 500 mg) were dried by a vacuum pump, followed by substituting with an argon gas. Dry toluene (5 ml) and dimethylsulfide (3.0 mmol) were added thereto and, after ice cooling, a solution of borane dimethylsulfide complex in toluene (1.07M, 0.65 ml, 0.7 mmol) was dropwise added. After stirring for two hours, an aqueous saturated ammonium chloride solution was added, followed by filtering through a cotton plug. The filtrate was washed with ethyl acetate and, after separating an aqueous layer, the organic layer was washed with 2NHCl, water, an aqueous saturated sodium hydrogen carbonate solution, water and saturated brine. After drying with anhydrous magnesium sulfate, the extract containing the titled compound as a main component was obtained by concentrating under a reduced pressure. The NMR chemical shifts of the titled compound are as follows.

1. filtrationby filtering through a cotton plug
2. washThe filtrate was washed with ethyl acetate
3. customafter separating an aqueous layer
4. washthe organic layer was washed with 2NHCl, water
5. dry with materialAfter drying with anhydrous magnesium sulfate
6. additionthe extract containing the titled compound as a main component
7. customwas obtained
8. concentrationby concentrating under a reduced pressure

ORD record

ord-fb051fc5d06644d7a20177fb8b85879c

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06049009