Diisobutylaluminum hydride → HCID 10073505, compound

Participants

Reaction Steps

Add DIBAL solution (5 mL, 1M/THF) dropwise to [6-hydroxy-2-(2-hydroxy-benzyl)-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (300 mg, 0.6 mmol) in THF (5 mL) at −78° C. Stir for 30 min and quench with water, followed by TFA (5 mL). Stir the mixture for 3 h while warming to r.t. Remove the solvent in vacuo and dissolve the residue in i-PrOH/CH2Cl2 (1:3). Wash the organic phase with water and brine, dry over MgSO4, filter and concentrate. Purify by flash chromatography (0-5% (2M NH3 in MeOH)/CH2Cl2) to afford 5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-6-oxa-12-thia-dibenzo[a,f]azulen-2-ol (180 mg, 62%).

Provenance & Evidence