Tetrahydrofuran → HCID 66809280, compound

Participants

Reaction Steps

To a four-necked two litter flask purged with nitrogen, 165.4 g (455.0 mmol) of diisobutyl 3-pyrrolylcyclohepta-2,7-diene-1,2-dicarboxylate obtained in Reference Example 2 and 1,158 mL of tetrahydrofuran were charged. Thereto, 500.0 mL (containing 455.0 mmol of borane-tetrahydrofuran complex) of a tetrahydrofuran solution (concentration: 0.91M) of a borane-tetrahydrofuran complex was added dropwise over 1.5 hour. The mixture was stirred for 6 hours at room temperature. The reaction mixture was provided with water, and the resultant mixture was subjected to toluene extraction. The extraction liquid was washed with water, and was dried over anhydrous magnesium sulfate. The dried liquid was filtered, and volatile matters contained therein were distilled away under reduced pressure to obtain orange colored oil. The oil was purified with silica-gel column chromatography (developing solvent: mixed solvent of 4 parts by volume of hexane with one part by volume of ethyl acetate), thereby obtaining 105.0 g (yield: 78.0%) of diisobutyl cyclohepta-2,7-diene-1,2-dicarboxylate as pale yellow oil with a purity of 99.6% determined by a gas chromatography measurement, its NMR and GCMS data being shown below:

Provenance & Evidence