6,6-diethoxy-2-methylhex-4-yn-3-one

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 6,6-Diethoxy-2-methyl-hex-4-yn-3-one (1.32 g, 6.66 mmol) in THF (20 ml) was cooled to 0° C. (ice bath). Methyl thioglycolate (0.6 ml, 6.66 mmol) was added in one portion and the mixture was stirred at 0° C. for 1 h. Methanol (3 ml) and Cs2CO3/MgSO4 (1 g/2 g, pre-dried at 200° C. in vacuum) were added at 0° C. The mixture was stirred at 0° C. for 15 min and then at rt for 15 h. The reaction mixture was quenched by pouring into EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 0-20% EtOAc in hexane to afford the desired product (0.58 g, 30% yield). The mixture was stirred at 0° C. for 15 min at rt for 15 h The reaction mixture was quenched by pouring into EtOAc The organic layer was washed with brine dried over Na2SO4 concentrated under reduced pressure The residue was purified by flash chromatography with 0-20% EtOAc in hexane

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

Procedure: 6,6-Diethoxy-2-methyl-hex-4-yn-3-ol (3.18 g, 18.46 mmol) was dissolved in dichloromethane (100 ml) and treated with activated MnO2 (30 g) at rt for 15 h. The reaction mixture was filtered through a plug of celite and Na2SO4. The filtrated was concentrated under reduced pressure and purified by flash chromatography with 0-15% EtOAc in hexane to afford the desired product (1.32 g, 36% yield). The reaction mixture was filtered through a plug of celite and Na2SO4 The filtrated was concentrated under reduced pressure purified by flash chromatography with 0-15% EtOAc in hexane