Tetrahydrofuran → HCID 66870587, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of hexyne (6.71 grams, 81.7 mmol) in THF (20 milliliters) in a 100 milliliter flask equipped with a condenser under an argon atmosphere were added dropwise 36 milliliters (72 mmol) of 2 M solution of isopropylmagnesium chloride in THF at room temperature. An exothermic reaction occurred upon addition. After addition, the reaction mixture was heated at 50° C. for 95 minutes and cooled down to room temperature. Benzo[1,2-b:4,5-b′]dithiophene-4,8-dione (3 grams, 13.6 mmol) was added, and the mixture was heated at 50° C. for 1 hour before cooling down to room temperature. Subsequently, a solution of 20 grams of SnCl2 in 50 milliliters 10 percent aq. HCl solution was added in a dropwise fashion followed by a further heating at 60° C. for 1 hour. After the reaction, the solvent was removed by vacuum evaporation, and the residue was purified by passing through a silica-gel flash column (eluent:hexane/dichloromethane, 2/1, v/v). Recrystallization of the crude product collected from flash chromatography from 2-propanol gave 3 grams (63 percent yield) of a red crystal after drying in vacuo.

Provenance & Evidence