Hydrochloric Acid → HCID 11475844, compound

Participants

Reaction Steps

To a solution of 208i (12.0 g, 20.3 mmol) in CH2Cl2 (200 mL) was added coned HCl (47 mL). The reaction mixture was stirred for 80 min at room temperature and diluted with water (200 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×70 mL). The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL), dried over anhydrous MgSO4, and concentrated in vacuo to yield the crude product (7.52 g). Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9) gave 209i (3.5 g, 40.0%) as a colorless oil. 1H NMR (CDCl3): 8 (ppm): 4.14 (q, J=7.1, 4 H), 2.41 (t, J=7.0, 4 H), 1.66-1.45 (m, 8 H), 1.35-1.20 (m, 12 H), 1.25 (t, J=7.1, 6 H), 1.17 (s, 12 H). 13C NMR (CDCl3): δ (ppm): 211.24, 177.89, 60.01, 42.69, 42.07, 40.64, 29.86, 29.07, 25.13, 24.73, 23.74, 14.24. HRMS (LSIMS, gly): Calcd for C25H47O5 (MH+): 427.3423, found: 427.3430.

Provenance & Evidence