DIETHYL 3-HYDROXYCYCLOBUTANE-1,1-DICARBOXYLATE synthesis

Yield:99974-66-0 97%

Reaction Conditions:

with hydrogen;palladium(II) hydroxide in ethanol;water at 20; for 8 h;

Steps:

Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate (3a)

Pd(OH)₂ (50% H₂O, 0.516 g, 15% w/w) was added to a solution of benzyl alcohol (1.70 g, 5.55 mmol) in EtOH (20 ml) and the reaction mixture was stirred at r.t. under H₂-atmosphere (60 psi) for 8 hours. The reaction mixture was filtered over Celite and the solvent was evaporated. The product was obtained as a colourless oil (1.17 g, 5.39 mmol, 97%) and used without further purification. ¹H-NMR data was consistent with literature.^{1 1}H-NMR (300 MHz, CDCl₃): 1.26 (6H, t, J 7.0, OCH₂CH₃), 2.17 (1H, br s, OH), 2.39-2.52 (2H, m, 2/4-H), 2.82-2.94 (2H, m, 2/4-H), 4.20 (4H, q, J 7.0, OCH₂CH₃), 4.30-4.45 (1H, m, 3-H); ¹³C-NMR (125 MHz, CDCl₃): 14.1 (OCH₂CH₃), 40.3 (C-2/4), 46.0 (C-1), 61.8 (C-3), 62.3 (OCH₂CH₃), 171.6 (C=O), 171.8 (C=O); LC-MS (m/z, ES⁺) 217.2 (30%, [M+H]⁺).

References:

Re?nik, Lisa-Maria;Cantelli, Christophe;Fersing, Cyril;Gongora, Céline;Pouget, Jean-Pierre;Lisowski, Vincent [Bioorganic and Medicinal Chemistry Letters,2020,vol. 30,# 22,art. no. 127527] Location in patent:supporting information