Diethyl Ether → HCID 88366201, compound

Participants

Reaction Steps

Diisobutylaluminum hydride (1.0M in hexanes, 1.54 mL, 1.54 mmol) was added dropwise to a solution of 26 (0.74 g, 1.18 mmol) in anhydrous diethyl ether (22 mL) at 0° C. under argon. The reaction mixture was allowed to warm to room temperature over 2.5 h. The reaction was quenched with ethyl acetate (2.5 mL) and 1N H2SO4 solution (5 mL) and stirring was continued for 10 min. The mixture was poured into a separatory funnel and the layers were separated. The aqueous layer was extracted again with diethyl ether. The organic layers were combined, washed sequentially with 1N NaOH solution and saturated sodium chloride solution, and concentrated in vacuo to give 0.72 g (97%) of 27 as a dark yellow oil. 1H NMR showed the presence of trace impurities, but the compound decomposed on silica gel. The material was used without purification in the next reaction. 1H NMR (300 MHz, CDCl3) δ9.73 (s, 1H, CHO), 7.61-7.77 (m, 4H, ArH), 7.03-7.42 (m, 13H, ArH), 5.62 (t, J=9 Hz, 1H, CH=C), 4.78 (s, 2H, CH2OSi), 3.66 (t, J=6 Hz, 1H, CHCHO), 2.92-3.01 (m, 1H, 1×CH2CH), 2.55-2.67 (m, 1H, 1×CH2CH), 1.95 (s, 3H, C=CCH3), 1.66 (s, 4H, CH2CH2), 1.28 (s, 12H, 4×CH3), and 1.07 (s, 9H, SiC(CH3)3).

Provenance & Evidence