Water → HCID 117396777, compound

Participants

Reaction Conditions

Reaction Steps

To 13.6 mL (32.6 mmol) lithium aluminum hydride solution (2.4 M in THF) are added dropwise 4.20 g (14.8 mmol) 1-benzyloxy-2-methoxy-3-(2-nitro-vinyl)-benzene (example X) in 20 mL THF at 0° C. After stirring at 0° C. for 2 h the reaction mixture is quenched by the addition of 0.59 mL (33 mmol) water, 8.20 mL (32.6 mmol) aq. NaOH solution (c=4 mol/L) and 1.80 mL (97.9 mmol) water. The resulting mixture is stirred for 20 min and filtered over celite/Na2SO4. The filtrate is concentrated by evaporation and the residue is purified by HPLC (ACN/H2O/NH4OH). After HPLC, ACN is removed in vacuo and the aq. layer is extracted with EtOAc. The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo.

Provenance & Evidence