2,2-dimethylcyclohexane-1,3-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,2-dimethylcyclohexane-1,3-dione (2.00 g, 14.3 mmol) in MeOH (20 mL) was added sodium borohydride (135 mg, 3.58 mmol) portion-wise at 0° C. The resulting solution was stirred at room temperature for 1 hour. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to afford the title compound (1.6 g, crude). MS (ESI) m/z 143.2 [M+H]+. The reaction was quenched with water the mixture was extracted with ethyl acetate The combined organic layers were washed with brine dried over anhydrous sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of cyclohexane-1,3-dione (10.0 g, 89.3 mmol), potassium carbonate (24.6 g, 178.6 mmol) and iodomethane (28.5 g, 201 mmol) in acetone (50 mL) was refluxed overnight. After completion, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (5-10% ethyl acetate in petroleum ether) to afford the title compound (3.5 g, 25.0 mmol, 28% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 2.69 (t, J=6.8 Hz, 4H), 1.52 (m, 2H) 1.31 (s, 6H). was refluxed overnight After completion, the solvent was removed under reduced pressure the residue was purified by silica gel column chromatography (5-10% ethyl acetate in petroleum ether)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,2-dimethylcyclohexane-1,3-dione (2.00 g, 14.3 mmol) in MeOH (20 mL) was added sodium borohydride (135 mg, 3.58 mmol) portion-wise at 0° C. The resulting solution was stirred at room temperature for 1 h. The reaction was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to afford the title compound (1.6 g, crude). MS (ESI) m/z 143.2 [M+H]+. The reaction was quenched with water extracted with ethyl acetate The combined organic layers were washed with brine dried over anhydrous sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of cyclohexane-1,3-dione (10.0 g, 89.3 mmol), potassium carbonate (24.6 g, 178.6 mmol), and iodomethane (28.5 g, 201 mmol) in acetone (50 mL) was refluxed overnight. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (5-10% ethyl acetate in petroleum ether) to afford the title compound (3.5 g, 25.0 mmol, 28% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 2.69 (t, J=6.8 Hz, 4H), 1.52 (m, 2H) 1.31 (s, 6H). was refluxed overnight The reaction mixture was concentrated the residue was purified by silica gel column chromatography (5-10% ethyl acetate in petroleum ether)