Aluminium lithium hydride → HCID 69640853, compound

Participants

Reaction Steps

A solution of 53.7 mg (0.125 mmol) of 56 in anhydrous Et2O (2 mL) was stirred at rt as 47.3 mg (1.25 mmol) of LiAlH4 was added and reaction was stirred at rt for 2 h. The reaction mixture was poured into saturated Na—K tartrate (100 mL) and extracted with EtOAc (3×, 70 mL). Combined organic extracts were dried over Na2SO4 and concentrated in vacuo giving 47.1 mg (87%) of 57 as a clear colorless oil which was a single isomer as judged by 1H NMR and used without further purification in the next step. Data for 57: TLC, T-2, Rf 0.31; 1H NMR (400 MHz, CDCl3) δ 0.88 (s, 3H, H-18), 1.05 (t, 1H, J=10.6 Hz, H-14), 3.38 (s, 3H, —CH2OCH3), 3.42 (dd, 1H, J=10.3, 8.2 Hz, CH2OH), 3.60 (t, 1H, J=8.9 Hz, H-17α), 3.78 (s, 3H, ArOCH3), 3.89 (dd, 1H, J=10.3, 3.2 Hz, —CH2OH), 4.66 & 4.69 (AB quartet, 2H, JAB=6.5 Hz, OCH2O), 6.62 (d, 1H, J=2.6 Hz, H-4), 6.72 (dd, 1H, J=8.7, 2.6 Hz, H-2), 7.22 (d, 1H, J=8.7 Hz, H-1).

Provenance & Evidence