Diisobutylaluminum hydride → HCID 86695166, compound

Participants

Reaction Steps

A solution of ethyl 2-[3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]acetate (2.88 g, 9.27 mmol, 1.00 equiv) in 25 mL of distilled THF was added DIBAL-H (25% in hexane, 10.56 g, 2.00 equiv) dropwise at −30° C. under nitrogen. The resulting solution was stirred for 2 h at this temperature and quenched with saturated aqueous NH4Cl, extracted with 3×100 mL of ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to afford 2.20 g (88%) of the desired 2-[3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]ethan-1-ol as a light yellow solid. MS: m/z 269, 270 [M+H]+.

Provenance & Evidence