Toluene → HCID 22004884, compound

Participants

Reaction Steps

To a solution of the intermediate obtained in Step C (37.3 g, 100 mmol) in anhydrous tetrahydrofuran (350 mL) stirred under argon at 0° C. was added a solution of 3.4M of sodium bis(2-methoxyethoxy)aluminum hydride in toluene (Red-Al) (105 mL, 204 mmol, 65 wt % in toluene) via syringe over 20 min. The reaction mixture was allowed to stir at room temperature for 24 hr, then cooled again to 0° C. and carefully quenched by the dropwise addition of water. The solution was decanted from the solid which forms and the solvent removed in vacuo. The residue was purified by flash chromatography (500 g silica) via step gradient. Elution with 5% diethyl ether/hexane affords 9.8 g (26.3 mmol, 28%) of recovered starting material and elution with 40% diethyl ether (Et2O)/hexane affords the desired product as a white solid (26.8 g, 77.8 mmol, 78%). mp 124-126° C. Rf=0.2 (10% ethyl acetate/hexane). 1H NMR (300 MHz, CDCl3): δ 7.35 (s, 1H), 7.27 (m, 2H), 7.08 (m, 2H), 4.44 (d, J=5.5 Hz, 2H), 3.43 (m, 4H), 2.92 (sept, J=6.6 Hz, 1H), 1.59 (s, 1H), 1.28 (m, 12H). FAB-MS: calculated for (C21H25FO3) 344, found 345 (M+H).

Provenance & Evidence