Aluminium lithium hydride → (S)-(1-(pent-4-en-2-yloxy)naphthalen-2-yl)methanol

Participants

Reaction Steps

To a mixture of (S)-methyl 1-(pent-4-en-2-yloxy)-2-naphthoate (300 mg, 1.110 mmol) in THF (10 mL) was added 1 N LAH (2.220 mL, 2.220 mmol) and the reaction was stirred at rt for 1 h. It was then quenched with NH4Cl and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to isolate (S)-(1-(pent-4-en-2-yloxy)naphthalen-2-yl)methanol (200 mg, 0.825 mmol, 74.4% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 8.19-8.08 (m, 1H), 7.90-7.80 (m, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.58-7.45 (m, 3H), 5.96 (ddt, J=17.1, 10.1, 7.2 Hz, 1H), 5.25-5.11 (m, 2H), 4.93 (qd, J=12.6, 5.9 Hz, 2H), 4.54-4.34 (m, 1H), 2.65 (qd, J=6.8, 5.5 Hz, 1H), 2.59-2.48 (m, 1H), 2.18 (t, J=6.0 Hz, 1H), 1.31 (d, J=6.4 Hz, 3H).

Provenance & Evidence