Aluminium lithium hydride → HCID 68503107, compound

Participants

Reaction Steps

Ester 10 (13.0 g, 18.5 mmol) and LiAlH4 (0.77 g, 20 mmol) in anhydrous THF (100 mL) were stirred at 0° C. for 1 hour. The reaction was quenched by the slow addition of H2O (20 mL). The reaction mixture was concentrated to approximately half volume and was then partitioned between EtOAc (250 mL) and water (500 mL). The aqueous phase was extracted with additional EtOAc (2×100 mL). The combined organic layers were dried over MgSO4 and concentrated to yield 10.82 g (87%) of 11 as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 6.56 (s, 2H), 4.58 (d, 2H, J=4.5 Hz), 3.99-4.07 (m, 6H), 3.76-3.82 (m, 6H), 1.98 (quint, 4H, J=6.0 Hz), 1.91 (quint, 2H, J=6.0 Hz), 0.87 (s, 18H), 0.86 (s, 9H), 0.03 (s, 12H), 0.02 (s, 6H); 13C NMR (75 MHz, CDCl3), δ 152.9, 136.9, 136.3, 104.9, 70.3, 65.4, 65.2, 60.3, 59.6, 33.5, 32.5, 25.8, 18.2, −5.4, −5.5; IR (film, NaCl) 3435 cm−1 (broad); High Resolution MS (electrospray), m/z 695.4178 (Calcd for C34H68O7Si3+Na+: 695.4171).

Provenance & Evidence