反应详情

温度

-78 °C

A 500 mL RB flask containing (3-chloro-5-fluorobenzyl)magnesium chloride, 0.25 M in diethyl ether (13040 μl, 3260 μmol) was allowed to stir at −78° C. for 5 minutes. At this time, TMEDA (492 μl, 3260 μmol) was added via a syringe and then THF (10 mL) was added via a syringe and the mixture was allowed to stir for 15 min before the addition of (S,E)-N-((S)-2,3-bis(tert-butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide (550.00 mg, 1304 μmol) (14 mL THF) via a syringe. The reaction was allowed to stir for 30 min and then quenched with ammonium chloride (sat, 100 mL). The aq. layer was extracted with EtOAc (3×100 mL). The combined organics were washed with brine and dried with sodium sulfate. The dried solution was filtered and concentrated to give 1.30 g of a crude oil that was purified on a 120 g ISCO column to give the title compound. Rf=0.40 in 20% EtOAc in hexanes.

1. stirringto stir for 30 min
2. customquenched with ammonium chloride (sat, 100 mL)
3. extractionThe aq. layer was extracted with EtOAc (3×100 mL)
4. washThe combined organics were washed with brine
5. dry with materialdried with sodium sulfate
6. filtrationThe dried solution was filtered
7. concentrationconcentrated
8. customto give 1.30 g of a crude oil that
9. customwas purified on a 120 g ISCO column