7-Nitro-1-tetralone → 7-Nitro-1,2,3,4-tetrahydronaphthalen-1-ol

Participants

Reaction Conditions

Reaction Steps

7-Nitro-3,4-dihydro-1(2H)-naphthalenone (5.0 g, 26.1 mmol) was stirred with 2M borane-dimethylsulfide in THF (14.4 mL, 28.8 mmol) in THF (200 mL) at rt for 15 h. The reaction was cooled to 0° C. and quenched with MeOH. The solvent and reaction byproducts were removed under vacuum and afforded 5.0 g (99%) of the desired alcohol as a brown powder. 1H NMR (400 MHz, DMSO-d6) δ 8.25 (d, J=2.6 Hz, 1 H), 7.98 (dd, J=8.5, 2.6 Hz, 1H), 7.34 (d, J=8.5 Hz, 1H), 5.55 (d, J=5.7 Hz, 1H), 4.63 (m, 1H), 2.87-2.73 (m, 2H), 2.00-1.83 (m, 2H), 1.75-1.60 (m, 2H).

Provenance & Evidence