Water → 3-(Cyclohexanecarbonyl)oxolan-2-one

Participants

Reaction Conditions

Reaction Steps

In a similar method as for example 7, the beta keto ester of alpha-cyclohexylcarbonyl-gamma-butyrolactone is prepared (see also compound IVa in Chem. Pharm. Bull. 37(4), 958-961, 1989 by Uchida et al.): methyl cyclohexanecarboxylate (30 g) and gamma-butyrolactone (26.7 g, 1.5 moleq.) are dissolved in 120 mL of dry dioxane and 20 mL of dry dimethyl sulfoxide. Sodium ethoxide (35.4 g, 2.5 moleq.) is added and the mixture is stirred overnight under N2 at a temperature of 100° C. The mixture is then cooled to ˜50-60° C. and ca. 400 mL H2O is added. The aqueous layer is brought to pH=6 with acetic acid, and is extracted with three 100 mL portions of chloroform (careful; CO2 formation). The organic layer is washed with H2O, thereafter with a NaHCO3-solution and finally with brine (a saturated NaCl solution), and is then dried with Na2SO4. Evaporation of the volatiles gives a ca. 85% yield of an oil. This crude beta-keto-ester (34 g) and guanidinium carbonate (31.2 g; 2 moleq. of guanidine) are stirred in ethanol (200 mL). To this mixture, that is heated to 50° C. and that is kept under an argon atmosphere, a 30 (w/w) % sodium methoxide solution in methanol (18.7 g of NaOMe in 65 mL of solution; 2 moleq. of NaOMe) is added drop wise. The mixture is heated overnight at an oil bath temperature of 90° C., is then evaporated down and water is added to the residue. The pH of the mixture is adjusted to 6 by addition of an HCl solution (careful; CO2 formation), and the resulting suspension is filtered. The residue is washed with several portions of water and dried in vacuo to give a white powder in a 70% yield. 1H NMR (200 MHz, DMSO-d6): δ 10.6 (1H), 6.2 (2H), 4.6 (1H), 3.3 (2H), 2.5 (3H), 2.0-1.0 (10H).

Provenance & Evidence