3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one

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

Procedure: Under an atmosphere of nitrogen, 441 mg (11.1 mmol, 2.06 equivalents) of an oily 60% sodium hydride was washed with dry hexane to remove paraffin. To this was added 6.0 ml of dry methanol cooling with ice and stirred. Then, a methanol (6.0 ml) solution of 1.135 g (5.400 mmol) of (2-methylpropyl) (2,4,6-trihydroxyphenyl) ketone (5) was added dropwise to the solution. Further, a methanol (5.0 ml) solution of 1.205 g (11.52 mmol, 2.130 equivalents) of 1-chloro-3-methyl-2-butene was slowly added dropwise. The mixture was stirred cooling with ice for 1.5 hours, then added 50 ml of a saturated aqueous ammonium chloride solution, and extracted from ether. The ether layer was washed with saturated brine, dried over sodium sulfate, and distilled under a reduced pressure to remove the solvent and obtain 1.752 g of a crude product in the form of a red viscous oily substance. This crude product was subjected to silica gel column chromatography (40 g of Wako Gel C-300 and eluted sequentially with 200 ml each of petroleum ether:ether at varying ratios=19:1, 18:2, 17:3, and 16:4). From the eluate of the column, various fractions were sequentially obtained. As the first fraction, 160 mg of {3,5-bis(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-methylpropyl) ketone (15) was obtained in the form of light yellow crystals shaped fine needles. Under an atmosphere of nitrogen, 441 mg (11.1 mmol, 2.06 equivalents) of an oily 60% sodium hydride was washed with dry hexane to remove paraffin To this was added 6.0 ml of dry methanol cooling with ice The mixture was stirred cooling with ice for 1.5 hours extracted from ether The ether layer was washed with saturated brine dried over sodium sulfate distilled under a reduced pressure to remove the solvent obtain 1.752 g of a crude product in the form of a red viscous oily substance and eluted sequentially with 200 ml each of petroleum ether From the eluate of the column, various fractions were sequentially obtained

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

Procedure: Under an atmosphere of nitrogen, 441 mg (11.1 mmol, 2.06 equivalents) of an oily 60% sodium hydride was washed with dry hexane to remove paraffin. To this was added 6.0 ml of dry methanol cooling with ice and stirred. Then, a methanol (6.0 ml) solution of 1.135 g (5.400 mmol) of (2-methylpropyl) (2,4,6-trihydroxyphenyl) ketone (5) was added dropwise to the solution. Further, a methanol (5.0 ml) solution of 1.205 g (11.52 mmol, 2.130 equivalents) of 1-chloro-3-methyl-2-butene was slowly added dropwise. The mixture was stirred cooling with ice for 1.5 hours, then added 50 ml of a saturated aqueous ammonium chloride solution, and extracted from ether. The ether layer was washed with saturated brine, dried over sodium sulfate, and distilled under a reduced pressure to remove the solvent and obtain 1.752 g of a crude product in the form of a red viscous oily substance. This crude product was subjected to silica gel column chromatography (40 g of Wako Gel C-300 and eluted sequentially with 200 ml each of petroleum ether:ether at varying ratios=19:1, 18:2, 17:3, and 16:4). From the eluate of the column, various fractions were sequentially obtained. As the first fraction, 160 mg of {3,5-bis(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-methylpropyl) ketone (15) was obtained in the form of light yellow crystals shaped fine needles. Under an atmosphere of nitrogen, 441 mg (11.1 mmol, 2.06 equivalents) of an oily 60% sodium hydride was washed with dry hexane to remove paraffin To this was added 6.0 ml of dry methanol cooling with ice The mixture was stirred cooling with ice for 1.5 hours extracted from ether The ether layer was washed with saturated brine dried over sodium sulfate distilled under a reduced pressure to remove the solvent obtain 1.752 g of a crude product in the form of a red viscous oily substance and eluted sequentially with 200 ml each of petroleum ether From the eluate of the column, various fractions were sequentially obtained

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

Procedure: Under an atmosphere of nitrogen, 441 mg (11.1 mmol, 2.06 equivalents) of an oily 60% sodium hydride was washed with dry hexane to remove paraffin. To this was added 6.0 ml of dry methanol cooling with ice and stirred. Then, a methanol (6.0 ml) solution of 1.135 g (5.400 mmol) of (2-methylpropyl) (2,4,6-trihydroxyphenyl) ketone (5) was added dropwise to the solution. Further, a methanol (5.0 ml) solution of 1.205 g (11.52 mmol, 2.130 equivalents) of 1-chloro-3-methyl-2-butene was slowly added dropwise. The mixture was stirred cooling with ice for 1.5 hours, then added 50 ml of a saturated aqueous ammonium chloride solution, and extracted from ether. The ether layer was washed with saturated brine, dried over sodium sulfate, and distilled under a reduced pressure to remove the solvent and obtain 1.752 g of a crude product in the form of a red viscous oily substance. This crude product was subjected to silica gel column chromatography (40 g of Wako Gel C-300 and eluted sequentially with 200 ml each of petroleum ether:ether at varying ratios=19:1, 18:2, 17:3, and 16:4). From the eluate of the column, various fractions were sequentially obtained. As the first fraction, 160 mg of {3,5-bis(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-methylpropyl) ketone (15) was obtained in the form of light yellow crystals shaped fine needles. Under an atmosphere of nitrogen, 441 mg (11.1 mmol, 2.06 equivalents) of an oily 60% sodium hydride was washed with dry hexane to remove paraffin To this was added 6.0 ml of dry methanol cooling with ice The mixture was stirred cooling with ice for 1.5 hours extracted from ether The ether layer was washed with saturated brine dried over sodium sulfate distilled under a reduced pressure to remove the solvent obtain 1.752 g of a crude product in the form of a red viscous oily substance and eluted sequentially with 200 ml each of petroleum ether From the eluate of the column, various fractions were sequentially obtained