Aluminium lithium hydride → HCID 71619143, compound

Participants

Reaction Steps

(—OH version of 19F-27): To a suspension of lithium aluminum hydride (4.1 g, 108 mmol) in THF solution (450 mL) at 0° C. was added dropwise compound 4 (40 g, 43.5 mmol) in THF (100 mL). Afterward, the solution was stirred overnight at room temperature and quenched with dilute HCl carefully, concentrated through rotary evaporation, and subjected to silica gel chromatography using hexane/EtOAc as the eluent to afford alcohol 5 (33.7 g, 39.7 mmol, 91% yield) as a clear oil: 1H NMR (500 MHz, CDCl3) δ 4.02 (s, 6H), 3.69 (t, J=6.0 Hz, 2H), 3.51 (t, J=4.5 Hz, 2H), 3.37 (s, 2H), 1.82-1.77 (m, 2H), 1.47 (s, 9H); 13C NMR (126 MHz, CDCl3) δ 120.4 (q, J=294.7 Hz), 80.1-79.4 (m), 69.3, 66.3, 66.7, 60.4, 46.4, 32.5; 19F NMR (470 MHz, CDCl3) δ—73.40 (s); MS (APCI) m/z 849 (M+H)+; HRMS (ESI) calcd for C20H16F27O5 849.0567 (M+H)+, 866.0832 [M+NH4]+. found 849.0577, 866.0811, respectively.

Provenance & Evidence