Cesium carbonate → 1-allyl-1-methyl-3,4-dihydronaphthalen-2(1H)-one

HRID 494625Notes

Reaction equation

HRID 494625 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

8

Reactant 4

HCID 10796Cesium carbonateHCID 11584Allyl acetateHCID 25517Ammonium ChlorideHCID 982091-Methyl-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 152546301-allyl-1-methyl-3,4-dihydronaphthalen-2(1H)-oneYield 90%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

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, 3H), 2.46 (m, 1H), 2.63 (m, 2H), 2.78 (m, 1H), 3.03 (m, 2H), 4.90 (m, 2H), 5.40 (m, 1H), 7.18 (m, 2H), 7.30 (m, 2H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. additionwith a mixture of 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-557ef21f7db144c8990e7b0f0ca778bd
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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