Aluminium lithium hydride → HCID 67483427, compound

Participants

Reaction Steps

The intermediate obtained in Step C (6 g, 12.35 mmol) was dissolved in anhydrous tetrahydrofuran (“THF”) (130 mL) under argon and treated dropwise at room temperature with lithium aluminum hydride (“LAH”)(1.0M in THF, 24.7 mL, 24.7 mmol). The reaction mixture was stirred at reflux for 3 hr, cooled to room temperature and quenched by the addition of 0.9 mL H2O, 0.9 mL 20% aqueous NaOH, and 2.7 mL H2O. The resulting suspension was filtered through a cake of Celite and the filtrate concentrated and purified by chromatography through silica (20% ethyl acetate/hexane) to afford 4.76 g of the title compound as a colorless wax. 1H NMR (300 MHz, CDCl3): δ 0.73-0.83 (m, 3 H), 1.37-1.70 (m, 14 H), 1.56 (s, 1 H), 1.92 (dq, J=0.90, 6.90 Hz, 2 H), 3.41 (δ, J=6.60, 13.20, 24.60 Hz, 2 H), 4.43 (d, J=5.1 Hz, 2 H), 5.10 (s, 2 H), 5.27-5.37 (m, 1 H), 5.97 (d, J=15.90 Hz, 1 H), 6.97-7.09 (m, 4 H), 7.35-7.48 (m, 5 H).

Provenance & Evidence