Diethyl Ether → HCID 19426785, compound

Participants

Reaction Steps

A solution of 2 g N-(6-isopropylbenzothiazol-2-yl)phenylalanine (5.9 mmol) in 60 mL THF was cooled on an ice-salt bath to -5° C., under nitrogen. A solution of 1.4N MeLi in ether (26 mL, 36.4mmol) was added via syringe over about one minute. After two hours 10 mL chlorotrimethylsilane (78 mmol) was added rapidly and the reaction warmed up to room temperature. The reaction was quenched with 1N HCl and the product extracted into ether, dried (Na2SO4) and concentrated. The product was purified by flash chromatography thru silica gel, eluting with CH2Cl2. Recrystallization from EtOH gave 0.75g product (2.2 mmol, 38%), mp 107°-110° C.

Provenance & Evidence