Tetrahydrofuran → HCID 11105650, 화합물

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CC1(C)[C@@H:6]([CH2:7][C:8]([OH:10])=[O:9])[C:5](=[O:11])OO1.[CH2:13]1[CH2:17][O:16]CC1.B.[CH2:19]1COCC1>CO>[OH:11][CH2:5][CH2:6][C@H:7]1[O:16][C:17]([CH3:13])([CH3:19])[O:10][C:8]1=[O:9]

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온도: 0 °C

실험 절차

To a stirring solution of (R)-(−)-dimethyl-5-oxo-1,2-dioxolane-4-acetic acid (15.8 g, 91 mmol), and THF (90 mL), at 0° C., under N2, was added borane-THF complex (1.0 M in THF, 100 mL, 100 mmol) dropwise over 60 minutes. The mixture was stirred at 0° C. for 2.5 hours and then allowed to warm to 25° C. The mixture was stirred at room temperature for 19 hours. The mixture was poured into MeOH (150 mL) and the solution was evaporated to dryness under reduced pressure at 25° C. The residue was purified via silica gel chromatography using 30% EtOAc in hexanes to obtain the desired alcohol as a clear oil (7.1 g, 44.6 mmol, 49% yield). 1H NMR (400 MHz, CDCl3) δ 4.61-4.51 (m, 1H), 3.89-3.80 (m, 2H), 2.20-2.12 (m, 2H), 2.05-1.98 (m, 1H), 1.64 (s, 3H), 1.57 (s, 3H).