Benzyl Bromide → 3-benzyloxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene

To 3-hydroxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (1.76 g, 10.0 mmol) dissolved in DMF (10 ml) were added potassium carbonate (2.76 g, 20.2 mmol) and benzyl bromide (1.308 ml, 11.0 mmol), and the resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, and the residue was mixed with water (20 ml) and extracted with ethyl acetate (20 ml×3). The combined organic layers were dried with anhydrous magnesium sulfate and were then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 35 g, ethyl acetate/hexane=1/9). The objective fractions were concentrated under reduced pressure to obtain 3-benzyloxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (2.79 g).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionthe residue was mixed with water (20 ml)
3. extractionextracted with ethyl acetate (20 ml×3)
4. dry with materialThe combined organic layers were dried with anhydrous magnesium sulfate
5. concentrationwere then concentrated under reduced pressure
6. concentrationThe objective fractions were concentrated under reduced pressure

ORD record

ord-14ec5e4291bc4ce9bd7d578089225eff

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627651B1