Chlorotrimethylsilane → HCID 67079336, compound

Participants

Reaction Conditions

Reaction Steps

After the reaction mixture was cooled to −48° C., the mixture was added dropwise to a solution of 3,4,5-tris(trimethylsilyloxy)-6-trimethylsilyloxymethyl-tetrahydropyran-2-one (402 g, 862 mmol) in tetrahydrofuran (2012 ml) at −77° C., and the reaction mixture was stirred at −70° C. for 1.5 hours. Triethylamine (24 ml, 172 mmol) and trimethylsilyl chloride (98 g, 903 mmol) were added thereto, and the mixture was warmed to 0° C. to give a solution containing 2,3,4,5-tetrakis(trimethylsilyloxy)-6-trimethylsilyloxymethyl-2-(5-bromo-2-(1-methoxy-1-methylethoxymethyl)phenyl)tetrahydropyran. The resulting solution was cooled to −78° C., and n-butyllithium in hexane (1.54 M, 1119 ml, 1724 mmol) was added dropwise thereto at the same temperature. After the mixture was stirred for 1 hour, 4-ethylbenzaldehyde (242 g, 1806 mmol) was added dropwise at −78° C., and the mixture was stirred at the same temperature for 2.5 hours. The reaction mixture was poured into an aqueous solution of 20% ammonium chloride, and the organic layer was separated, and washed with water. The solvent was evaporated under reduced pressure to give a product containing the titled compound as an oil (879 g). The product was used in the next step without further purification.

Provenance & Evidence