Chlorotrimethylsilane → HCID 22616363, compound

To a solution of 2,2-dimethyl-7-methoxy-1,3-benzodioxole-4-carbaldehyde (9.3 g, 45 mmol) obtained by the method mentioned in the Japanese Published Unexamined Patent Application No. 98/147585 and by a method similar thereto in acetonitrile (47 mL) was added lithium bromide (8.9 g, 85 mmol), and then trimethylsilyl chloride (8.5 mL, 67 mmol) was added dropwise. After 15 minutes, the mixture was ice-cooled, and 1,1,3,3-tetramethyldisiloxane (13 mL, 76 mmol) was added dropwise, followed by stirring at room temperature for 2 hours. The resulting mixture was diluted with toluene and filtered through Celite. The solvent was evaporated in vacuo from the filtrate to give a pale yellow oil. To a solution of this crude 7-bromomethyl-2,2-dimethyl-4-methoxy-1,3-benzodioxole in DMF (73 mL) was added sodium cyanide (5.0 g, 102 mmol), and the mixture was stirred at room temperature for18 hours. Under ice-cooling, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=5/1) to give Compound 12a (9.1 g, 92%) as an ash-colored solid.

1. temperaturecooled
2. filtrationfiltered through Celite
3. customThe solvent was evaporated in vacuo from the filtrate
4. customto give a pale yellow oil
5. stirringthe mixture was stirred at room temperature for18 hours
6. temperatureUnder ice-cooling
7. extractionthe mixture was extracted with ethyl acetate
8. washThe organic layer was washed with brine
9. dry with materialdried over sodium sulfate
10. customthe solvent was evaporated in vacuo
11. customThe residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=5/1)

ORD record

ord-2ff3d7fda20445b58837280d3a5e9f48

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06376535B2