Acetonitrile → HCID 21996517, compound

To a solution of 1,1,1,3,3,3-hexamethyldisilazane (4.74 g, 29.4 mmol) in THF (30 ml) was gradually added dropwise, at −78° C., a butyllithium hexane solution (1.56 M hexane solution, 18.8 ml, 29.4 mmol). The mixture was stirred for 10 minutes, to which was then added acetonitrile (1.41 ml, 26.9 mmol). The reaction mixture was stirred for further 20 minutes, to which was then added dropwise a solution of 7-methoxy-2,2-dimethyl-1-tetralone (5.0 g, 24.5 mmol) in THF (10 ml), followed by stirring for 2 hours. The reaction mixture was poured into water, and the organic layer was subjected to extraction with chloroform. The extract solution was washed with brine and water, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8) to give the above-titled compound (5.3 g, yield 88%).

1. stirringThe reaction mixture was stirred for further 20 minutes, to which
2. stirringby stirring for 2 hours
3. extractionthe organic layer was subjected to extraction with chloroform
4. washThe extract solution was washed with brine and water, which
5. dry with materialwas dried over anhydrous magnesium sulfate
6. distillationby distilling off the solvent under reduced pressure
7. customThe residue was purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8)

ORD record

ord-ab852d761f4944b580046057f01c4636

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235789B1