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ChemicalBook CAS DataBase List Diethyl squarate
5231-87-8

Diethyl squarate synthesis

7synthesis methods
-

Yield:5231-87-8 97%

Reaction Conditions:

in ethanol at 80; for 48 h;

Steps:

2.2.8 Synthesis of 2-diethoxy-1-cyclobutene-3,4-dione

To a stirred solution of 3,4-dihydroxycyclobut-3-ene-1,2-dione (3.00g, 26.4mmol) in anhydrous ethanol (150mL) was added triethyl orthoformate (72.2mmol, 12.0mL) at room temperature. The mixture was heated to reflux at 80°C and left for 48h before being concentrated under reduced pressure. The crude yellow oil was purified by flash chromatography (DCM) to yield the title compound (3.57g, 97%) as an intensely yellow oil which was not purified further; 1H NMR (300MHz, CDCl3): δ 4.72 (m, 4H), 1.44 (t, J=87.9Hz, 6H). Data are in agreement with that previously reported [43].

References:

Ryan, Philip;Shi, Yun;von Itzstein, Mark;Rudrawar, Santosh [Bioorganic Chemistry,2021,vol. 110,art. no. 104738]

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