Reaction #3759628
Related Literature (1)
openreactiondata ↗doi:10.6084/m9.figshare.5104873.v1; patent:US08097758B2
Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1.46 ml of thionyl chloride (20 mmol) were added to a solution of 1.38 g of 3-(2-furyl)acrylic acid (10 mmol) in 10 ml of chloroform and 0.1 ml of DMF. The solution was warmed to 70° C. and kept at this temperature for 1 h, then the solvents were removed under reduced pressure and the residue was dissolved in 6.6 ml of DCM and 3.3 ml of pyridine and subsequently cooled to 0° C. 0.96 ml of 2-propanol (12.5 mmol) was added, the temperature was increased to RT and the reaction mixture was stirred for 2.5 h. It was acidified with 30 ml of 1 M hydrochloric acid and extracted with 150 ml of ethyl acetate. The organic phase was washed with aqueous sodium hydrogencarbonate solution, dried over sodium sulfate, filtered and the solvents were removed under reduced pressure. 1.72 g (yield: 96%) of the title compound were obtained. LC/MS (Method D) (M+H-isopropyl)+ 139 the solvents were removed under reduced pressure the residue was dissolved in 6.6 ml of DCM 3.3 ml of pyridine and subsequently cooled to 0° C the temperature was increased to RT extracted with 150 ml of ethyl acetate The organic phase was washed with aqueous sodium hydrogencarbonate solution dried over sodium sulfate filtered the solvents were removed under reduced pressure
Source ID: ord-9be70656195b4bdda623c09e30b4d6b4