1,1-Dichloroethane → HCID 66906414, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C., copper (I) iodide (4.11 g, 21.6 mmol) was dissolved in diethyl ether (10 mL). Methyllithium (1.6N, 27 mL) was added and the mixture was stirred for 10 minutes. The solvent was removed under reduced pressure and cold dichloromethane (10 mL) was added. The solvent was removed under reduced pressure. Cold dichloroethane (83 mL) was added and the mixture was cooled to −78° C. Trimethylsilyl chloride (2.73 mL, 21.6 mmol) was added, followed by a solution of ethyl 3-{3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]phenyl}but-2-enoate (2.43 g, 5.4 mmol) and dichloroethane (10 mL). The temperature was maintained at 0° C. for 3 hrs and the mixture was then hydrolyzed with saturated aqueous ammonium chloride. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 95/5) to yield 2.6 g (84%) of the desired product as an oil.

Provenance & Evidence