Reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1.Cl.[C:15](=O)([O:18]C)[O:16][CH3:17]>>[C:15]([CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:12][CH2:13][C:4]1=[O:3])([O:16][CH3:17])=[O:18]Participants
Procedure
To a suspension of sodium hydride (60% oil dispersion, 4.8 g gross) in dimethyl carbonate (150 mL) stirring at room temperature under argon, was added 2-oxo-1,2,3,4-tetrahydronaphthalene (14.6 g). The resulting mixture was then refluxed for 30 min before cooling to 0° C. Once at the prescribed temperature and while maintaining inert atmosphere, 2.0 M aqueous hydrochloric acid solution (200 mL) was added slowly. Upon completion of the addition, the reaction mixture was extracted with ethyl acetate (three times). The combined extracts were dried over anhydrous magnesium sulfate and evaporated under vacuum to yield a residue. The residue was purified by silica gel chromatography eluting with 15% ethyl acetate in hexane to obtain the title compound (16.9 g).
Workup
- temperatureThe resulting mixture was then refluxed for 30 min
- temperaturebefore cooling to 0° C
- additionwas added slowly
- additionUpon completion of the addition
- extractionthe reaction mixture was extracted with ethyl acetate (three times)
- dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
- customevaporated under vacuum
- customto yield a residue
- customThe residue was purified by silica gel chromatography
- washeluting with 15% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-3d886df4f88b4c09bfd9550d2455ea2f
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07214704B2
Linked notes
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