Triethylamine → HCID 86593288, compound

Participants

Reaction Steps

To a solution of 4-[[[tert-butyl(dimethyl)silyl]oxy]methyl]-8,8-dimethyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ol (28.90 g, 86.38 mmol), triethylamine (24.1 ml, 173 mmol) and 4-N,N-dimethylaminopyridine (1.06 g, 8.64 mmol) in acetonitrile (100 ml) was dropwise added a solution of methanesulfonyl chloride (14.8 g, 130 mmol) in acetonitrile (10 ml) under ice-cooling. Lithium chloride (5.49 g, 130 mmol) was added thereto, and the mixture was stirred at room temperature for 6 hrs. The reaction solution was poured into water and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in N,N-dimethylformamide (100 ml), and 1,8-diazabicyclo[5.4.0]-7-undecene (25.8 ml, 173 mmol) was added. The mixture was stirred at 80° C. overnight. The reaction solution was-poured into water and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to give the objective substance.

Provenance & Evidence