Sodium ethoxide → HCID 178525776, compound

Participants

Reaction Steps

A mixture of cis/trans-4-(tetrahydro-pyran-4-yloxy)-cyclohexanecarboxylic acid ethyl ester (7:1) (0.385 g, 1.50 mmol) and sodium ethoxide (0.204 g, 3.00 mmol) in dry toluene (1.5 ml) was heated at reflux for 20 h. The reaction mixture was cooled to room temperature, diluted with 1,4-dioxane (7.5 ml) and 2 M aqueous sodium hydroxide solution (7.5 ml). Stirring for 16 h was followed by partitioning between 2 M aqueous sodium hydroxide solution (50 ml) and dichloromethane. The layers were separated. The aqueous layer was extracted with one portion of dichloromethane. The combined organic layers were washed with two 50 ml portions of 2 M aqueous sodium hydroxide solution. The combined aqueous layers were acidified to pH 1 by addition of concentrated hydrochloric acid solution (100 ml). The aqueous layer was extracted with two 150-ml portions of dichloromethane. The combined organic layers from the acidic extraction were dried over anhydrous sodium sulfate and dried in vacuo to give the title compound (0.358 g, 93%) as yellow solid. MS m/e: 229 (M+H+)

Provenance & Evidence