methyl 4-hydroxyhex-2-ynoate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of methyl-4-hydroxy-2-hexynoate (25.0 g, 176 mmol) in acetone (200 mL), cooled in an ice water bath, was added Jones reagent (70 mL of 3.2 M chromium VI oxide in 1:3 sulfuric acid:water). The reaction mixture was allowed to stir at room temperature for 3 h then filtered through a plug of diatomaceous earth and the filter cake was rinsed with dichloromethane (2×100 mL). The organic phase was saved and the aqueous phase was extracted with dichloromethane (2×100 mL). The combined organic phases were washed with saturated sodium bicarbonate (2×200 mL), dried (sodium sulfate) and concentrated to provide 17.0 g (69%) of 4-oxo-hex-2-ynoic acid methyl ester. then filtered through a plug of diatomaceous earth the filter cake was rinsed with dichloromethane (2×100 mL) the aqueous phase was extracted with dichloromethane (2×100 mL) The combined organic phases were washed with saturated sodium bicarbonate (2×200 mL) dried (sodium sulfate) concentrated

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

Procedure: To a solution of methyl-4-hydroxy-2-hexynoate (25.0 g, 176 mmol) in acetone (200 mL), cooled in an ice water bath, was added Jones reagent (70 mL of 3.2 M chromium VI oxide in 1:3 sulfuric acid:water). The reaction mixture was allowed to stir at room temperature for 3 h then filtered through a plug of diatomaceous earth and the filter cake was rinsed with dichloromethane (2×100 mL). The organic phase was saved and the aqueous phase was extracted with dichloromethane (2×100 mL). The combined organic phases were washed with saturated sodium bicarbonate (2×200 mL), dried (sodium sulfate) and concentrated to provide 17.0 g (69%) of 4-oxo-hex-2-ynoic acid methyl ester. then filtered through a plug of diatomaceous earth the filter cake was rinsed with dichloromethane (2×100 mL) the aqueous phase was extracted with dichloromethane (2×100 mL) The combined organic phases were washed with saturated sodium bicarbonate (2×200 mL) dried (sodium sulfate) concentrated

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 4-Hydroxy-hex-2-ynoic acid methyl ester (1.50 g, 10.55 mmol) in dichloromethane (30 mL) was added Des-martin periodinane (6.0 g, 14.14 mmol) and stirred at room temperature for 18 hours. Additional periodinane (4.5 g) was added to the reaction mixture and stirred at room temperature for 6 hours. Aqueous NaHCO3 was added to reaction mixture, and precipitate was filtered and washed with dichloromethane. Aqueous phase was extracted with dichloromethane, and combined organic phase was washed with water, brine, dried over Na2SO4, filtered and concentrated under vacuum to afford 1.48 g (100%) of title compound. C7H8O3 (140.04) Additional periodinane (4.5 g) was added to the reaction mixture stirred at room temperature for 6 hours was filtered washed with dichloromethane Aqueous phase was extracted with dichloromethane, and combined organic phase was washed with water, brine dried over Na2SO4 filtered concentrated under vacuum

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

Procedure: To a solution of methyl-4-hydroxy-2-hexynoate (25.0 g, 176 mmol) in acetone (200 mL), cooled in an ice water bath, was added Jones reagent (70 mL of 3.2 M chromium VI oxide in 1:3 sulfuric acid:water). The reaction mixture was allowed to stir at room temperature for 3 h then filtered through a plug of diatomaceous earth and the filter cake was rinsed with dichloromethane (2×100 mL). The organic phase was saved and the aqueous phase was extracted with dichloromethane (2×100 mL). The combined organic phases were washed with saturated sodium bicarbonate (2×200 mL), dried (sodium sulfate) and concentrated to provide 17.0 g (69%) of 4-oxo-hex-2-ynoic acid methyl ester. then filtered through a plug of diatomaceous earth the filter cake was rinsed with dichloromethane (2×100 mL) the aqueous phase was extracted with dichloromethane (2×100 mL) The combined organic phases were washed with saturated sodium bicarbonate (2×200 mL) dried (sodium sulfate) concentrated