Lithium Hydroxide → HCID 19002307, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 42 (536 mg, 1.15 mmol) in THF (10 mL) at 0° C. was added 0.2 N LiOH (6.3 mL, 1.3 mmol, 1.1 equivalents) at 0° C. dropwise over 15 minutes. The reaction was then stirred at 0° C. and monitored by TLC with four additions of 576 μL (0.115 mmol, 0.1 equivalents) 0.2 N LiOH over a 2 hour period. The reaction mixture was then partitioned between ice-cold 0.2 N HCl/brine and EtOAc (3×75 mL); dried (MgSO4) and solvent removed by rotovap (20° C.) to yield 33 as a foam (500 mg, 96%). 1H NMR (250 MHz, CDCl3 +D2O) δ:7.46 (d, 2H, J=8.1 Hz, aromatic), 7.21 (d, 2H, J=8.1 Hz, aromatic), 4.57 (m, 1H, Hα), 4.10 (m, 4H, OCH2), 3.11 (m, 2H, Hβ), 1.36 (s, 9H, C(CH3)3), 1.23 (2 t, 6H, J=7.1 Hz, CH3); FABMS m/z 452.1 (M+H)+.

Provenance & Evidence