Potassium Carbonate → methyl 2-(2,4-difluorobenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

To methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (327 mg, 1.50 mmol) dissolved in DMF (6 ml) were added potassium carbonate (415 mg, 3.00 mmol) and 2,4-difluorobenzyl bromide (0.212 ml, 1.65 mmol), and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure, ethyl acetate (40 ml) was added to the residue and the resulting mixture was washed with water (5 ml×2) and an aqueous saturated solution of sodium chloride (5 ml). The organic layer was dried with anhydrous magnesium sulfate and was then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 15 g, ethyl acetate/hexane=1/25). The objective fractions were concentrated under reduced pressure to obtain methyl 2-(2,4-difluorobenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (500 mg, 1.45 mmol, 97%).

1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate (40 ml)
2. additionwas added to the residue
3. washthe resulting mixture was washed with water (5 ml×2)
4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
5. concentrationwas then concentrated under reduced pressure
6. concentrationThe objective fractions were concentrated under reduced pressure

ORDレコード

ord-48d7f40183b54dda80ae667162b41e89

出典データセット

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06627651B1