Cesium carbonate → 1-allyl-1-methyl-3,4-dihydronaphthalen-2(1H)-one
Reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=O.C([O:16][CH2:17][CH:18]=[CH2:19])(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[CH2:3]([C:2]1([CH3:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:16][CH2:17][C:18]1=[O:19])[CH:4]=[CH2:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 1-methyl-2-tetralone (10.0 g, 62.4 mmol), allyl acetate (7.42 mL, 68.7 mmol), cesium carbonate (20.3 g, 62.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.143 g, 0.156 mmol), 1,2-diaminocyclohexane-N,N′-bis(2′-diphenylphosphinobenzoyl) (0.215 g, 0.312 mmol) in tetrahydrofuran (300 mL) was bubbled a stream of nitrogen through the mixture for ten minutes. The solution was then stirred at room temperature for 4 days followed by the addition of ethyl acetate (200 mL) and a saturated aqueous solution of ammonium chloride. The organic layer was separated, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography employing 70-230 mesh silica gel eluting with a mixture of 10% ethyl acetate in hexane to provide the title compound as a light yellow oil (10.07 g, 90%). 1H NMR (300 MHz, CDCl3): δ 1.43 (s, 3 H), 2.46 m, 1 H), 2.63 m, 2 H), 2.78 m, 1 H), 3.03 m, 2 H), 4.90 m, 2 H), 5.40 m, 1 H), 7.18 (m, 2 H), 7.30 m, 2 H).
Workup
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography
- additionwith a mixture of 10% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-d93c0938f83b4610807b02ad78249145
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07378414B2
Reaction notes
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