Hydrochloric Acid → HCID 11441998, compound

Participants

Reaction Steps

In analogy to the procedure of 214g, to a solution of 207h (18.0 g, 63.1 mmol), tetrabutylammonium iodide (2.0 g, 5.4 mmol) and TosMIC (4.8 g, 24.6 mmol) in anhydrous DMSO (250 mL) and Et2O (80 mL) was added NaH (60% dispersion in mineral oil, 2.5 g, 62.5 mmol) while cooling with an ice bath under N2 atmosphere. After 24 h at room temperature, the mixture was hydrolyzed and worked up by extraction to give the crude intermediate (18.0 g) as a brown oil. This crude material was heated to reflux in methanol (300 mL), concd HCl (36 mL) and water (70 mL) for 3 h. Extractive workup and purification by flash chromatography (silica gel; hexanes/ethyl acetate/hexanes=10/1, 5/1, 2/1) yielded 214h (6.1 g, 56%) as a yellowish oil. 1H NMR (CDCl3): δ 7.32-7.19 (m, 10 H), 3.68 (d, 2 H, J=10.8), 3.50 (d, 2 H, J=10.8), 2.26 (t, 4 H, J=7.50 H), 1.88-1.42 (m, 10 H), 1.25 (s, 6 H), 1.22-0.85 (m, 8 H). 13C NMR (CDCl3): δ 211.68, 144.94, 128.56, 126.82, 126.23, 72.68, 43.50, 42.79, 38.42, 30.01, 23.74, 23.68, 21.62. HRMS (LSIMS, nba): Calcd for C29H43O3 (MH+): 439.3212, found: 439.3207. HPLC: 95.3% pure.

Provenance & Evidence