Lithium hydroxide, monohydrate → HCID 11206816, compound

Participants

Reaction Steps

To a solution of 5-cyclohex-1-enyl-5-methyl-4-oxo-4,5-dihydro-furan-2-carboxylic acid methyl ester (47 mg, 0.2 mmol) in THF/MeOH (1/1, 2 mL) was added LiOH.H2O (8.4 mg, 0.2 mmol). The reaction mixture was stirred at room temperature for 5 hours. After concentration, the residue was dissolved in H2O (4 mL), washed with ethyl ether (2×5 mL). The separated aqueous layer was acidified to pH 2. This acidified solution was extracted with ethyl ether (3×5 mL). The extracts were dried (Na2SO4), filtered and concentrated. The crude product was purified with a silica gel column using EtOAc/AcOH (20/1) providing 35 mg (79%) of racemic 5-cyclohex-1-enyl-5-methyl-4-oxo-4,5-dihydro-furan-2-carboxylic acid: LC-MS m/z 221 (M−1); 1H NMR (400 MHz, CDCl3) δ 6.30 (s, 1H), 5.90 (m, 1H), 2.16-2.06 (m, 3H), 1.79-1.70 (m, 1H), 1.67-1.51 (m, 4H), 1.58 (s, 3H).

Provenance & Evidence