Oxalic acid dihydrate → HCID 86731005, compound

Participants

Reaction Steps

Oxalic acid dihydrate (68 g, 0.54 mol) was added to a solution of 2-[3-(methoxymethylidene)cyclobutyl]propan-2-ol (70 g, 0.45 mol) in THF:H2O (1:1, 700 mL) at 0° C. and stirred at ambient temperature for 1 hour. Then, 10% aqueous NaHCO3 solution was added to the reaction mixture and extracted with EtOAc (500 mL×4). The combined organic layer was then washed with water (200 mL×2), brine (200 mL) dried over anhydrous Na2SO4 and concentrated in vacuo to afford the title compound as a pale yellow liquid (mixture of cis and trans isomers). 1H NMR (400 MHz, CDCl3, mixture of cis and trans): δ 1.09-1.11 (2 s, 6H), 2.07-2.26 (m, 4H), 2.31-2.39 (m, 1H), 2.95-2.99 (m, 1H), 9.75 & 9.84 (2 s, 1H). 13C NMR (100 MHz, CDCl3, mixture of cis and trans): δ 21.8, 26.1, 39.4, 40.7, 41.8, 70.3, 202.6. 1H NMR (400 MHz, DMSO-d6, mixture of cis and trans): δ 0.96 (s, 3H), 0.98 (s, 3H), 1.88-2.29 (m, 5H), 2.87-2.92 (m, 1H), 4.13 & 4.21 (2 s, 1H), 9.56 & 9.74 (2 s, 1H). 13C NMR (100 MHz, DMSO-d6, mixture of cis and trans): 22.1, 22.7, 26.8, 40.9, 41.9, 42.4, 68.8, 69.1, 203.8, 204.1. 1H NMR (400 MHz, DMSO-d6-D2O exchange, mixture of cis and trans): δ 0.94 (s, 3H), 0.96 (s, 3H), 1.85-2.22 (m, 5H), 2.86-2.90 (m, 1H), 9.53 & 9.71 (2 s, 1H).

Provenance & Evidence