Aluminium lithium hydride → HCID 69216097, compound

Participants

Reaction Steps

A mixture of Example 695D (6.32 g, 20 mmol) in 100 mL of THF was treated with 1.0 M LiAlH4 in THF (35 mL, 35 mmol) at 0° C. The reaction mixture was stirred for additional 30 minutes, quenched with MeOH, and concentrated under vacuum. The residue was partitioned between ethyl acetate and pH=3 water. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 1:9 hexanes/ethyl acetate to provide 5.18 g (90%) of the desired product. MS (DCI) m/e 289 and 291 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 9.83 (s, 1H), 7.96 (s, 1H), 7.67 (d, J=8.5 Hz, 1H), 7.06 (d, J=2.0 Hz, 1H), 6.91 (dd, J=8.5, 2.0 Hz, 1H), 6.81-6.84 (m, 3H), 4.59 (t, J=6.0 Hz, 1H), 3.51-3.53 (m, 2H), 2.58 (t, J=6.9 Hz, 2H).

Provenance & Evidence