Diisobutylaluminum hydride → HCID 69583696, compound

Participants

Reaction Steps

To a solution of ethyl 6-[3-bromo-4,5-methylenedioxyphenyl]-2-naphthoate (18.32 g, 45.90 mmol) in 308 mL toluene at −78° C. under an atmosphere of argon was added DIBAL (92 mL, 1.5 M in toluene, 137.7 mmol) dropwise. After 1 hour the reaction mixture was quenched with ethyl acetate and the resulting mixture was allowed to warm to RT. The mixture was diluted with ethyl acetate and washed with 5% NH4Cl, water and brine. The organics were dried with magnesium sulfate, filtered and evaporated. The residue was passed through a short silica gel column (eluent: CH2Cl2) to give 16.40 g of 6-[3-bromo-4,5-methylenedioxyphenyl]-naphthalen-2-yl-methyl alcohol (100%). 1H NMR (300 MHz; CDCl3): δ 4.85 (s, 2H), 6.01 (s, 2H), 6.88 (s, 1H), 7.13 (s, 1H), 7.47 (dd, J1=4.0 Hz, J2=1.8 Hz, 1H), 7.50 (dd, J1=4.0 Hz, J2=1.8 Hz, 1H), 7.76–7.85 (m, 4H).

Provenance & Evidence