Tributylamine → HCID 86618521, Verbindung

To a flask was added ethyl 2-(3-chlorophenyl)-2-oxoacetate (1.8 g, 8.47 mmol) and acetic anhydride (1.60 ml, 16.93 mmol) in DCE (5 ml) at RT. To the resulting solution was added titanium(IV) chloride (16.93 ml, 16.93 mmol) and tributylamine (2.42 ml, 10.16 mmol). The solution was heated to reflux for 12 hours. The solution was then cooled in ice, and a solution of ammonium chloride was added. The mixture was stirred for 30 min. LC/MS indicated all starting material was gone. The solution was washed with 1×NH4Cl, 1N HCl, water, dried and concentrated in vacuo to provide 3-(3-chlorophenyl)furan-2,5-dione which was used as is in the next reaction. LC/MS, m/e 209 (M+1). HPLC Rt, 2.89 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min. hold at 100% B 1 min, flow rate 4 mL/min.

1. temperatureThe solution was heated
2. temperatureto reflux for 12 hours
3. temperatureThe solution was then cooled in ice
4. washThe solution was washed with 1×NH4Cl, 1N HCl, water
5. customdried
6. concentrationconcentrated in vacuo

ORD-Eintrag

ord-bcc4d356e4914ac38c1ce5bab8aa2622

Quelldatensatz

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07723336B2