Diisopropylamine → HCID 86604548, compound

Participants

Reaction Steps

A solution of 1.57 M n-BuLi in hexane (0.17 mL) was added dropwise to a solution of diisopropylamine (31 mg, 0.36 mmol) in tetrahydrofuran (1.8 mL) at −78° C., followed by stirring at the same temperature for 20 min. To the resulting solution, a solution of 1,3-benzothiazol-2-ylnonylsulfone (44 mg, 0.14 mmol) in tetrahydrofuran (1 mL) at −78° C., followed by stirring at the same temperature for 30 min. 0.6 mL of the resulting solution (which corresponds to 8.8 mg, 0.027 mmol of the anion of 1,3-benzothiazol-2-ylnonylsulfone) was added to asolution of (8E,12E)-7-acetoxy-3,6-bis(1-ethoxyethoxy)-6,10,12-trimethyl-14-oxotetradeca-8,12-dien-11-olide (6.9 mg, 0.013 mmol) in tetrahydrofuran (0.5 mL) at −78° C. The temperature of the resulting solution was gradually (during one hour 50 min.) raised to room temperature with stirring. A saturated aqueous ammonium chloride solution was added to the reaction mixture and the mixture was further diluted with ethyl acetate. Then, the mixture was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The resulting crude product was purified by silica gel column chromatography (Kanto silica gel 60N, spherical, neutral, 40 to 100 μm, eluate; hexane:ethyl acetate=80:20) to give the title compound (3.2 mg, 38%) as a pale yellow oil.

Provenance & Evidence