Hydrochloric Acid → HCID 19372339, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.3 g (0.9 mmol) of 1-vinyl-3-carbomethoxy-6benzyloxynaphthalene and 0.9 ml (0.9 mmol) of 1.0M BH3.THF complex in 15 ml of THF is stirred at 25° C. for 2 hours. To this is added 1 ml of H2O, 1 ml of 1N NaOH and 1 ml of 30% H2O2 which is then stirred at 25° C. for 2 hours. The mixture is acidified to pH ~1 using 1N HCl and extracted with ethyl acetate. The organics are dried (MgSO4) and concentrated in vacuo. Purification by flash silica gel chromatography using 15% ethyl acetate in hexanes as an eluent affords 0.08 g of 1-hydroxyethyl-3-carbomethoxy-6-benzyloxynaphthalene in the form a yellow oil which is used directly in the next step.

Provenance & Evidence