Methyl 2-(2,2-dichloro-3-oxocyclobutyl)acetate → Methyl 2-(3-oxocyclobutyl)acetate

Temperature

100 °C

To a solution of (2,2-dichloro-3-oxo-cyclobutyl)-acetic acid methyl ester (2.93 g, 13.8 mmol) in AcOH (100 ml), zinc powder (4.51 g, 69.0 mmol) is added. The mixture is stirred at 100° C. for 15 hours. The mixture is filtrated and washed with AcOH. The filtrate is concentrated under reduced pressure, and the residue is dissolved in AcOEt, and washed with saturated aqueous NaHCO3 and brine. The organic layer is dried over MgSO4, and concentrated under reduced pressure to give (3-oxo-cyclobutyl)-acetic acid methyl ester (710 mg, 36%); 1H NMR (400 MHz, chloroform-d) δ ppm 2.64-2.66 (m, 2H), 2.78-2.86 (m, 3H), 3.22-3.32 (m, 2H), 3.70 (s, 3H).

1. filtrationThe mixture is filtrated
2. washwashed with AcOH
3. concentrationThe filtrate is concentrated under reduced pressure
4. dissolutionthe residue is dissolved in AcOEt
5. washwashed with saturated aqueous NaHCO3 and brine
6. dry with materialThe organic layer is dried over MgSO4
7. concentrationconcentrated under reduced pressure

ORD record

ord-e4b53ae896d4475ba9c7e5fdbd6f796c

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193349B2