Isopropanol → HCID 11412914, compound

Temperature

90 °C

A 15 mL screw top test tube fitted with a PTFE septum cap was purged with argon before addition of CuI (5.0 mg, 0.026 mmol, 2.6 mol %) and NaOH (83.0 mg, 2.08 mmol). 2-(aminoethyl)-ethanol (101 μL, 1.04 mmol), 2-iodoanisole (162 μL, 1.25 mmol) and isopropyl alcohol (1.0 mL) were added, via syringe, under argon. The septum cap was replaced with a solid, Teflon-lined cap and the reaction was stirred magnetically at 90° C. for 48 h. The resulting homogeneous solution was allowed to cool before dilution with 10 mL brine. The reaction mixture was transferred to a separatory funnel and extracted with methylene chloride (3×10 mL). The organics were washed with 0.1 M NaOH (2×10 mL), washed with brine (1×15 mL), dried over MgSO4 and concentrated. The crude material was purified by silica gel chromatography using methylene chloride/ethyl acetate (70:30). The product was obtained as a pale yellow, viscous oil in 72% yield (145.8 mg).

1. customcap
2. customThe septum cap
3. customlined cap
4. customThe reaction mixture was transferred to a separatory funnel
5. extractionextracted with methylene chloride (3×10 mL)
6. washThe organics were washed with 0.1 M NaOH (2×10 mL)
7. washwashed with brine (1×15 mL)
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customThe crude material was purified by silica gel chromatography
11. customThe product was obtained as a pale yellow, viscous oil in 72% yield (145.8 mg)

ORD record

ord-04094fba05784de7b2314b6f1b815a75

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06759554B2