Pyridine → HCID 89676698, compound

Participants

Reaction Steps

At 23° C., a flask containing (S)-2-(1-(1-chloro-3-methylnaphthalen-2-yl)-2-(trityloxy)ethoxy)-2-methylpropan-1-ol (1.31 g, 2.21 mmol) was charged with Ac2O (5.00 mL) immediately followed by pyridine (5.00 mL). 4-(N,N-dimethylamino)-pyridine (20 mg, 0.164 mmol) was added. After 1.5 h, the reaction was poured onto 50 mL of crushed ice and H2O. A white precipitate developed. EtOAc (50 mL) was added after several hours had passed. Solid NaHCO3 was added portionwise (bubbling) until the aq. layer had a pH of 9. The slurry was extracted with EtOAc (2×25 mL). The combined organic layers were washed with 1.0 M aq. CuSO4 monohydrate (3×25 mL) and H2O (25 mL). The final organic phase was dried over Na2SO4, filtered, and concentrated. The residue was treated with benzene and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give (S)-2-(1-(1-chloro-3-methylnaphthalen-2-yl)-2-(trityloxy)ethoxy)-2-methylpropyl acetate. 1H NMR (400 MHz, CDCl3) δ 8.25 (d, J=8.6 Hz, 1H), 7.68 (d, J=7.8 Hz, 1H), 7.52-7.41 (m, 9H), 7.26-7.16 (m, 9H), 5.99 (dd, J=8.2, 4.7 Hz, 1H), 4.02 (app. s, 2H), 3.55 (dd, J=8.6, 8.4 Hz, 1H), 3.12 (dd, J=9.8 Hz, 4.7 Hz, 1H), 2.52 (s, 3H), 1.86 (s, 3H), 1.32 (s, 3H), 1.15 (s, 3H).

Provenance & Evidence