Water → Cyclobutylidene-acetic acid ethyl ester

Temperature

0 °C

To a solution of triethyl phosphono acetate (35.2 g) in 100 mL THF, at 0° C., was added slowly via a syringe a solution of NaH (6.2 g) in 60 mL THF. The mixture was stirred at 0° C. for 10 minutes, cyclobutanone (10 g) was added by a syringe, and the resulting mixture was stirred at room temperature for 2 hours, followed by addition of distilled water to quench the reaction. The aqueous solution was extracted by ethyl acetate (3×20 mL), the combined organic layers were dried over Na2SO4 and the solvent was removed by evaporation. The crude residue was eluted by column chromatography (10% ethyl acetate/hexane), to give ethyl 2-cyclobutylideneacetate (20 g). 1HNMR (300 MHz, CDCl3) δ=5.57 (s, 1H), 4.13 (q, 2H), 3.11 (m, 2H), 2.81 (m, 2H), 2.08(m, 2H), 1.26 (t) ppm. MS: m/z 370 (100, M+H)+

1. stirringthe resulting mixture was stirred at room temperature for 2 hours
2. customto quench
3. customthe reaction
4. extractionThe aqueous solution was extracted by ethyl acetate (3×20 mL)
5. dry with materialthe combined organic layers were dried over Na2SO4
6. customthe solvent was removed by evaporation
7. washThe crude residue was eluted by column chromatography (10% ethyl acetate/hexane)

ORD record

ord-a78fd826fe0949d7ba9316365716d6bd

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576094B2