Diisobutylaluminum hydride → 6-[3-(1-Adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylalcohol

Participants

Reaction Steps

To a solution of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthaldehyde (0.500 g, 1.26 mmol, see Example 9) in 15 mL toluene at −78° C. under an atmosphere of argon was added DIBAL (2.5 mL, 1.0 M in toluene, 3.79 mmol) via needle 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 1.0 N HCl, water and brine. The organics were dried with magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: CH2Cl2) to give 0.450 g of 6-[3-(1-adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylalcohol (90%), mp 169–171° C. 1HNMR (300 MHz; CDCl3): δ 1.80 (s, 6H), 2.10–2.18 (m, 9H), 3.90 (s, 3H), 4.86 (s, 2H), 6.98 (d, J=8.4 Hz, 1H), 7.24–7.25 (m, 1H), 7.46–7.59 (m, 3H), 7.71–7.74 (m, 1H), 7.80–7.89 (m, 3H), 7.97 (s, 1H).

Provenance & Evidence