Methyl Acrylate → HCID 21867438, compound

Participants

Reaction Steps

To a solution of the ester from Step 3 (0.5 g, 1.76 mmol) in toluene (7 mL) and THF (1 mL) at RT was added 1M potassium t-butoxide (1.76 mL, 1.76 mmol). After 15 minutes, methyl acrylate (0.32 mL, 3.5 mmol) was added, and the mixture was brought to reflux for 1.5 hours. The reaction was quenched by the addition of saturated NH4Cl solution, and the product was extracted with EtOAc/THF. The organic layer was washed with H2O and brine, dried (MgSO4), filtered, and evaporated. The intermediate was suspended in EtOH (10 mL), and concentrated HCl (2 mL) was added. After heating to reflux for 2 hours, the mixture was cooled and diluted with H2O (30 mL). The product was extracted with CH2Cl2 and the organic phase was washed with H2O before drying (MgSO4). Following filtration and removal of solvent under vacuum, the product was stirred with 1:2 EtOAc:hexane to give a tan-coloured solid (0.4 g).

Provenance & Evidence