Triethylamine → HCID 22349419, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-Bromomethyl-4-(4-methoxy-phenoxy)-benzoic acid methyl ester (0.2 grams, 0.57 mmol) and 3 mL of ethanol was added ethoxyethylamine (0.073 mL, 0.062 grams, 0.70 mmol) and triethylamine (0.098 mL, 0.071 grams, 0.7 mmol). After shaking for 4 hours at 50° C., the mixture was cooled to room temperature and concentrated under a stream of nitrogen. The residue was treated with methanesulfonic acid (3 mL) and methionine (0.13 grams). The mixture was shaken for 24 hours at room temperature and was then heated to 50° C. for 6 hours. After cooling to room temperature, the mixture was poured into aqueous 5 M sodium hydroxide with cooling in an ice bath, and the pH was adjusted to 8 with aqueous sodium bicarbonate. The aqueous phase was extracted 3 times with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Purification by radial chromatography (2 mm silica gel plate) eluting with 3% methanol-methylene chloride afforded 30 miligrams of 2-(2-Ethoxy-ethyl)-5-(4-hydroxy-phenoxy)-2,3-dihydro-isoindol-1-one as a colorless syrup. MS: 314.3 [M+H]+

Provenance & Evidence