Triethylamine → HCID 12129258, compound

Participants

Reaction Steps

To a suspension of 7-hydroxyquinoline (2.240 g, 15.43 mmol) in dry CH2Cl2 (30 mL) were added (in this order) DMAP (94 mg, 0.77 mmol), triethylamine (4.3 mL, 3.1 g, 31 mmol), and TBDMSCl (2.558 g, 16.97 mmol), and the mixture was stirred overnight at ambient temperature. Water and sat. NH4Cl sol. (10 mL each) were added, the layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×30 mL). The combined organic layers were washed with 0.25 M citric acid (2×), water, sat. NaHCO3 solution, and brine, and dried over MgSO4. EtOAc (10 mL) was added to the solution, which was then filtered through a silica gel plug (60 mL glass frit filled ≈½ with silica gel) and concentrated to give the title compound as pale yellow oil. The material thus obtained was used without further purification; 1H NMR (CDCl3, 400 MHz) δ 0.29 (s, 6H), 1.03 (s, 9H), 7.15 (dd, J=2.8, 8.8 Hz, 1H), 7.26 (dd, J=4.0, 8.0 Hz, 1H), 7.46 (d, J=2.8 Hz, 1H), 7.70 (d, J=8.8 Hz, 1H), 8.08 (dd, J=0.8, 8.0 Hz, 1H), 8.83 (dd, J=1.6, 4.0 Hz, 1H); MS (ES+): m/z 260.2 (100) [MH+]; HPLC: tR=3.8 min (OpenLynx, polar—5 min).

Provenance & Evidence