1-Bromohexadecane → (R)-2-Phenyl-(S)-4-hexadecyloxymethyl-1,3dioxane

Participants

Reaction Steps

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.

Provenance & Evidence