反应详情

To a suspension of NaH (3 g, 60% in mineral oil) in 30 mL of dry THF was added a solution of (R)-2-phenyl-(S)-4-hydroxymethyl-1,3-dioxane (1.47 g, 7.6 mmol) in 10 mL of THF at 0° C. After 30 min, hexadecyl bromide (3 mL, 9.88 mmol) and tetrabutylammonium iodide (0.28 g, 0.76 mmol) were added. After the mixture was stirred overnight, the reaction was quenched by addition of 5 mL of MeOH. The solvent was removed under reduced pressure, and ether and water were added. The product was extracted with ether. The organic layer was dried over Na2SO4 and concentrated. The product was purified by column chromatography on silica gel, eluting with EtOAc-PE (5%) to afford 1.55 g (50%) of 6 as a white solid; mp 51-54° C. MS: m/z 441 (M++Na+), (calcd. for C27H45O3, 418.662). 1H NMR (300 MHz, CDCl3): δ7.51-7.31 (m, 5H, Ph), 5.54 (s, PhCH—), 4.32-4.27 (m, —CHO), 4.10-3.94 (m, 2H, —CH2O—), 3.65-3.59 (m, 4H, —CH2O), 1.89-1.83 (m, 2H, —CH2—), 1.62-1.54 (m, 2H), 1.25 (s, 26H), 0.88 (t, 3H, CH3). 13C-NMR (CDCl3, 75 MHz): δ139.28, 129.32, 128.77, 126.79, 101.88, 77.09, 74.44, 72.61, 67.61, 32.74, 30.51, 30.30, 30.18, 29.18, 26.93, 23.51, 14.94.

1. customthe reaction was quenched by addition of 5 mL of MeOH
2. customThe solvent was removed under reduced pressure, and ether and water
3. additionwere added
4. extractionThe product was extracted with ether
5. dry with materialThe organic layer was dried over Na2SO4
6. concentrationconcentrated
7. customThe product was purified by column chromatography on silica gel
8. washeluting with EtOAc-PE (5%)