Water → HCID 86707789, compound

Participants

Reaction Steps

To a solution of 3-(4-Diethoxymethyl-phenyl)-3-hydroxy-cyclobutanecarboxylic acid ethyl ester (Preparation 1, 7 g, 21.73 mmol) in EtOH:H2O (80 mL, 1:1) was added sodium acetate (3.2 g, 39.31 mmol) followed by hydroxylamine hydrochloride (2.24 g, 32.60 mmol) at 0° C. Resulting reaction mixture was stirred at room temperature for 16 hours. After consumption of starting material, reaction mixture was concentrated in vacuo and diluted with water (70 mL). Aqueous layer was extracted with EtOAc (3×70 mL). Combined organic layer was dried over sodium sulphate, filtered and evaporated under reduced pressure to afford crude residue. Crude was purified by column chromatography on silica gel (100-200 mesh size). Compound was eluted using 40% ethyl acetate in hexane to afford yellowish oil (4.7 g, 87%). 1H NMR and LC-MS was consistent. 1H NMR (400 MHz, DMSO-d6) δ: 1.19 (t, J=7.16 Hz, 3H), 2.60-2.65 (m, 2H), 2.78-2.82 (m, 1H), 4.07 (q, J=7.1 Hz, 2H), 7.50-7.50 (m, 4H), 8.12 (s, 1H), 11.18 (s, 1H). LCMS (m/z): 246.10 (M+H).

Provenance & Evidence