Ethyl Acetate → HCID 89525845, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 265A (2.4 g, 9 mmol) in pyridine (50 mL) was added POCl3 (8.4 mL, 90 mmol) dropwise and the solution was stirred at 60° C. for 12 hours. Pyridine was removed under reduced pressure and the solution was basified with 1 N NaOH. The aqueous layer was extracted with EtOAc (25 mL×3). The combined organic phases were washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography eluted with petroleum ether:ethyl acetate=20:1 to obtain the title compound (2.6 g, 44.3% yield) as a colorless oil. 1H NMR: (400 MHz, CDCl3): δ 5.80 (d, J=9.6 Hz, 1H), 4.26-4.17 (m, 4H), 2.66-2.59 (m, 2H), 2.45-2.38 (m, 2H), 2.34-2.24 (m, 1H), 2.10-2.00 (m, 1H), 1.49 (s, 9H).

Provenance & Evidence