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ChemicalBook CAS DataBase List 2,3-DIHYDRO-2,2-DIMETHYLINDEN-1-ONE
10489-28-8

2,3-DIHYDRO-2,2-DIMETHYLINDEN-1-ONE synthesis

13synthesis methods
-

Yield:17496-14-9 450 mg ，10489-28-8 900 mg

Reaction Conditions:

with n-butyllithium in tetrahydrofuran at 0; for 1 h;

Steps:

T-27 Example T-27: Alkylation alpha to a ketone

To a solution of 2,3-dihydro-1H-inden-1-one (2 g, 15.13 mmol) in THF (50 mL) was added iodomethane (2.15 g, 15.13 mmol) and butyllithium (0.97 g, 15.13 mmol). The reaction mixture was cooled to 0 °C and stirred at that temperature for 1 h. Na2S2O3 (20 mL) was added to the reaction vessel and was extracted with DCM (3 x 15 ml). The layers were separated and the organic phase was washed with saturated aqueous NaCl (2 x 15 mL). The combined organics were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. After concentration, the residue was purified by silica column chromatography with a gradient elution of hexane to hexane (90%) and EtOAc (10%) to give the product 2-methyl-2,3-dihydro-1H-inden-1-one (450 mg, 3.08 mmol) and 2,2-dimethyl-2,3- dihydro-1H-inden-1-one (900 mg, 5.62 mmol) as a yellow oil.

References:

WO2018/26371,2018,A1 Location in patent:Paragraph 0220

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