Sodium hydride → HCID 16086969, compound

Participants

Reaction Steps

To a suspension of sodium hydride (60% in mineral oil; 77.1 mg, 1.93 mmol) in anhydrous n-Bu2O (5 ml) 15a (500 mg, 1.75 mmol) is added batch wise, and the mixture is stirred for an additional two hours at RT. Then, 6-bromohexanoic acid chloride (0.314 ml, 2.10 mmol) is added, and the reaction is heated for 4 h under reflux. The mixture is allowed to cool to RT, poured into ice-water, and extracted with CH2Cl2. The organic phases are unified, washed with a saturated solution of NaHCO3 (2×) and saturated NaCl, and dried over MgSO4. Finally, the solvent is distilled off, and the crude product is crystallized from methanol. 713 mg (88%) of the desired compound 19a are obtained as a colorless solid. Melting point. 133-135° C.; IR (KBr) 2920, 1700, 1645, 1580 cm−1; 1H-NMR (CDCl3) δ 8.06 (d, 8.6 Hz, 4H), 7.30 (d, 8.6 Hz, 4H), 3.92 (s, 6H), 3.38 (t, 6.7 Hz, 2H), 2.29 (t, 7.4 Hz, 2H), 1.88-1.77 (m, 2H), 1.76-1.64 (m, 2H), 1.49-1.35 (m, 2H); MS (FD) m/z 464 (M++1 for Br81), 462 (M++1 for Br79).

Provenance & Evidence