Triethylamine → HCID 12129258, compound

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).

1. customthe layers were separated
2. extractionthe aqueous layer was extracted with CH2Cl2 (2×30 mL)
3. washThe combined organic layers were washed with 0.25 M citric acid (2×), water, sat. NaHCO3 solution, and brine
4. dry with materialdried over MgSO4
5. additionEtOAc (10 mL) was added to the solution, which
6. filtrationwas then filtered through a silica gel plug (60 mL glass frit
7. additionfilled ≈½ with silica gel) and
8. concentrationconcentrated

ORD record

ord-ba1f1405edcd45b08550f1efe038b788

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653268B2