Tetrahydrofuran → 3-(6-Benzyloxynaphthalen-2-yl)pentan-3-ol

Participants

Reaction Steps

Cool 6-benzyloxynaphthalene-2-carboxylic acid methyl ester (5.75 g, 19.67 mmol) in THF (115 mL) to about 0° C. and treat the solution dropwise with ethyl magnesium bromide (23.0 mL, 69.0 mmol, 3.0 M in ether). Allow the reaction to warm to RT and stir it for 3 h. Quench with water and concentrate. Dissolve the crude residue in CH2CL2 (200 mL), wash twice with brine, dry over Na2SO4 and filter. Concentrate the filtrate to give the title compound as a yellow solid (6.0 g, 95%). MS (ES) m/e 321 (M+1).

Provenance & Evidence