Water → HCID 66740277, compound

Participants

Reaction Conditions

Reaction Steps

One third of the 3 g of ethyl [4-(4-trifluoromethanesulfonyloxyphenyl)cyclohexyl]acetate (3 g, 7.61 mmol, 1 eq.) is placed, respectively, in one third of the 18 mL of dioxane in three 20 mL microwave tubes. One third of each amount of the reagents molybdenum hexacarbonyl (1 g, 3.80 mmol, 0.5 eq.), 0.171 g of palladium acetate (II) (0.76 mmol, 0.1 eq.), 0.422 g of 1,1′-bis(diphenylphosphino)ferrocene (0.76 mmol, 0.1 eq.), 1.859 g of 4-dimethylaminopyridine (15.21 mmol, 2 eq.), 3.1 mL of diisopropylethylamine (17.49 mmol, 2.3 eq.) and 2.74 mL of water is successively and respectively added to each tube. The tubes are heated at 120° C. for 20 minutes in a Biotage microwave machine. The reaction media are filtered through Celite. The filtrate is diluted with 200 mL of dichloromethane and washed with twice 100 mL of saturated sodium carbonate solution. 10 mL of ethyl ether are added. After separation of the phases by settling, the aqueous phase is acidified to pH=1 with 5N hydrochloric acid solution and extracted with twice 200 mL of dichloromethane. The organic phase is concentrated to dryness to give 0.560 g of 4-(4-ethoxycarbonylmethylcyclohexyl)benzoic acid.

Provenance & Evidence