Water → HCID 11137304, compound

Participants

Reaction Steps

To a solution of commercial (4S,5R)-methyl 2,2,5-trimethyl-1,3-dioxolane-4-carboxylate (2.5 g, 14.4 mmol) in CH2Cl2 (50 ml) at 0° C. was added 1M LiAlH4/THF (35.9 ml, 35.9 mmol). After stirring overnight at RT and cooling to 0° C., EtOAc (5.0 mL) was added. Stirring was continued at RT for 30 min prior to addition of water (50 mL); whereupon, the aqueous mixture was extracted with EtOAc (2×100 mL). The combined organic extracts were washed with sat'd NaCl, dried (Na2SO4), and concentrated. Chromatography (SiO2 230-400 mesh, Hex to 85/15 Hex/EtOAc) of the crude product afforded the expected alcohol (1.18 g, 56% yield) as a clear liquid: 1H NMR δ (CDCl3) 4.02 (m, 1H), 3.81 (dd, J=12.1, 2.8 Hz, 1H), 3.65 (m, 1H), 3.60 (dd, J=12.1, 4.4 Hz, 1H), 1.43 (s, 1H), 1.40 (s, 3H), 1.29 (d, J=6.1 Hz, 3H).

Provenance & Evidence