Diisobutylaluminum hydride → HCID 22041389, compound

Participants

Reaction Steps

To a slurry of 6-trifluoromethanesulfonyloxy-naphthalene-2-carboxylic acid ethyl ester (136.50 g, 0.392 mol) in toluene (1.0 L) at −70° C. was added a solution of DIBAL (1.5 M, 5.75 mL, 0.862 mol) dropwise while maintaining an internal temperature below −55° C. The resulting mixture was allowed to stir for 1 hour and subsequently quenched with acid to pH 5–6 while warming to room temperature. The mixture was extracted with ether (2×). The organics were combined, washed with water (3×), brine and dried (MgSO4). After filtering, the solvents were evaporated and the crude material was purified on silica (eluent: hexane:CH2Cl2, 1:1 to 100% CH2Cl2) to afford 86.0 g (72%) of 6-trifluoromethanesulfonyloxy-naphthalen-2-yl-methanol as an off-white solid. 1H NMR (300 MHz; CDCl3) 2.31 (brs, 1 H), 4.83 (s, 2 H), 7.34 (dd, J1=9.0 Hz, J2=2.0 Hz, 1 H), 7.51 (dd, J1=8.4 Hz, J2=2.0 Hz, 1 H), 7.71 (d, J=2.0 Hz, 1 H), 7.75–7.90 (m, 3 H).

Provenance & Evidence