Ethylene Glycol → HCID 21940656, Verbindung

Temperatur

75 °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 %), K3PO4 (425 mg, 2.0 mmol), rac-2-amino-1-phenylethanol (140 mg, 1.02 mmol) and 1-iodo-3-nitrobenzene (302 mg, 1.25 mmol). Ethylene glycol (56 μL, 1.02 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 75° C. for 48 h. The reaction mixture was allowed to cool before dilution with 10 mL brine and extraction with methylene chloride (3×10 mL). The organic extracts 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 (96:4). The product was obtained as an orange, viscous oil in 66% yield (172.8 mg).

1. customcap
2. customThe septum cap
3. customlined cap
4. washThe organic extracts were washed with 0.1 M NaOH (2×10 mL)
5. washwashed with brine (1×15 mL)
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe crude material was purified by silica gel chromatography
9. customThe product was obtained as an orange, viscous oil in 66% yield (172.8 mg)

ORD-Eintrag

ord-0a22fd608ba346cf8dec645905c37b92

Quelldatensatz

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09067955B2