Aluminium lithium hydride → 3-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]propan-1-ol

Participants

Reaction Steps

To a suspension of lithium aluminium hydride (1.40 g, 35.6 mmol) in anhydrous tetrahydrofuran (100 mL) was added dropwise a tetrahydrofuran solution (30 mL) of ethyl 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate (6.00 g, 29.7 mmol) at 0° C. under nitrogen. The reaction mixture was stirred at room temperature overnight, then quenched with the addition of water (1.4 mL) and 10% aqueous sodium hydroxide (1.4 mL). The white solid was removed by filtration, and the filtrate was concentrated in vacuo. The residue was partitioned between water (50 mL) and ethyl acetate (50 mL). The organic phase was washed with brine, dried (sodium sulfate), and concentrated in vacuo to afford the title compound. 1H NMR (300 MHz, CDCl3): δ 4.03-4.13 (m, 2H), 3.65-3.69 (m, 2H), 3.50-3.55 (m, 1H), 1.61-1.69 (m, 4H), 1.32 (s, 3H), 1.24 (s, 3H).

Provenance & Evidence