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

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).

1. customquenched with the addition of water (1.4 mL) and 10% aqueous sodium hydroxide (1.4 mL)
2. customThe white solid was removed by filtration
3. concentrationthe filtrate was concentrated in vacuo
4. customThe residue was partitioned between water (50 mL) and ethyl acetate (50 mL)
5. washThe organic phase was washed with brine
6. dry with materialdried (sodium sulfate)
7. concentrationconcentrated in vacuo

ORD record

ord-f401e00101b54f679455018b6ffaf53c

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07880014B2