(2S)-6-甲基庚-2-醇

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium hydride (60% dispersion in mineral oil, 2.9 g, 72 mmol) and dimethylformamide (100 mL) were charged to a 250 mL three-necked flask fitted with thermocouple, magnetic stirrer, condenser and dropping funnel. To the reaction mixture was added a solution of (2S)-6-methylheptan-2-ol (3.1 g, 24 mmol) in dimethylformamide (10 mL). This reaction mixture was stirred at room temperature for 1 hr then allyl bromide (8.6 g, 72 mmol) was added dropwise over 10 minutes ensuring the reaction temperature did not rise significantly (41° C. was observed). The reaction mixture was stirred for a further 20 minutes until the reaction was complete. To the reaction mixture was added water (10 mL) and the resultant mixture was extracted with methyltert-butyl ether (2×100 mL). The combined organic phase was dried over magnesium sulphate and the solvent remove in vacuo to yield a yellow oil which was chromatographed over silica gel (hexane/methyltert-butyl ether) to give 3-{[(1S)-1,5-dimethylhexyl]oxy}prop-1-ene as a sl. yellow oil (2.7 g, 15.8 mmol, chemical yield 66%). fitted with thermocouple, magnetic stirrer, condenser rise significantly (41° C. was observed) The reaction mixture was stirred for a further 20 minutes until the reaction the resultant mixture was extracted with methyltert-butyl ether (2×100 mL) The combined organic phase was dried over magnesium sulphate the solvent remove in vacuo to yield a yellow oil which was chromatographed over silica gel (hexane/methyltert-butyl ether)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5% Palladium on carbon (0.02 g), (2S)-6-methylhept-5-en-2-ol (4.0 g, 3 mmol) and methanol (20 mL) were added to a 50 mL round-bottomed flask fitted with a magnetic stirrer. The flask was evacuated and then pressurised with 1 bar of hydrogen from a balloon. This was repeated three times then the reaction mixture was stirred for 8 hours at room temperature under hydrogen. The crude reaction mixture was filtered and the solvent removed in vacuo to yield (2S)-6-methylheptan-2-ol (3.4 g, 26 mmol, chemical yield 85%), suitable for the next stage. fitted with a magnetic stirrer The flask was evacuated The crude reaction mixture was filtered the solvent removed in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium hydride (60% dispersion in mineral oil, 2.9 g, 72 mmol) and dimethylformamide (100 mL) were charged to a 250 mL three-necked flask fitted with thermocouple, magnetic stirrer, condenser and dropping funnel. To the reaction mixture was added a solution of (2S)-6-methylheptan-2-ol (3.1 g, 24 mmol) in dimethylformamide (10 mL). This reaction mixture was stirred at room temperature for 1 hr then allyl bromide (8.6 g, 72 mmol) was added dropwise over 10 minutes ensuring the reaction temperature did not rise significantly (41° C. was observed). The reaction mixture was stirred for a further 20 minutes until the reaction was complete. To the reaction mixture was added water (10 mL) and the resultant mixture was extracted with methyltert-butyl ether (2×100 mL). The combined organic phase was dried over magnesium sulphate and the solvent remove in vacuo to yield a yellow oil which was chromatographed over silica gel (hexane/methyltert-butyl ether) to give 3-{[(1S)-1,5-dimethylhexyl]oxy}prop-1-ene as a sl. yellow oil (2.7 g, 15.8 mmol, chemical yield 66%). fitted with thermocouple, magnetic stirrer, condenser rise significantly (41° C. was observed) The reaction mixture was stirred for a further 20 minutes until the reaction the resultant mixture was extracted with methyltert-butyl ether (2×100 mL) The combined organic phase was dried over magnesium sulphate the solvent remove in vacuo to yield a yellow oil which was chromatographed over silica gel (hexane/methyltert-butyl ether)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5% Palladium on carbon (0.02 g), (2S)-6-methylhept-5-en-2-ol (4.0 g, 3 mmol) and methanol (20 mL) were added to a 50 mL round-bottomed flask fitted with a magnetic stirrer. The flask was evacuated and then pressurised with 1 bar of hydrogen from a balloon. This was repeated three times then the reaction mixture was stirred for 8 hours at room temperature under hydrogen. The crude reaction mixture was filtered and the solvent removed in vacuo to yield (2S)-6-methylheptan-2-ol (3.4 g, 26 mmol, chemical yield 85%), suitable for the next stage. fitted with a magnetic stirrer The flask was evacuated The crude reaction mixture was filtered the solvent removed in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium hydride (60% dispersion in mineral oil, 2.9 g, 72 mmol) and dimethylformamide (100 mL) were charged to a 250 mL three-necked flask fitted with thermocouple, magnetic stirrer, condenser and dropping funnel. To the reaction mixture was added a solution of (2S)-6-methylheptan-2-ol (3.1 g, 24 mmol) in dimethylformamide (10 mL). This reaction mixture was stirred at room temperature for 1 hr then allyl bromide (8.6 g, 72 mmol) was added dropwise over 10 minutes ensuring the reaction temperature did not rise significantly (41° C. was observed). The reaction mixture was stirred for a further 20 minutes until the reaction was complete. To the reaction mixture was added water (10 mL) and the resultant mixture was extracted with methyltert-butyl ether (2×100 mL). The combined organic phase was dried over magnesium sulphate and the solvent remove in vacuo to yield a yellow oil which was chromatographed over silica gel (hexane/methyltert-butyl ether) to give 3-{[(1S)-1,5-dimethylhexyl]oxy}prop-1-ene as a sl. yellow oil (2.7 g, 15.8 mmol, chemical yield 66%). fitted with thermocouple, magnetic stirrer, condenser rise significantly (41° C. was observed) The reaction mixture was stirred for a further 20 minutes until the reaction the resultant mixture was extracted with methyltert-butyl ether (2×100 mL) The combined organic phase was dried over magnesium sulphate the solvent remove in vacuo to yield a yellow oil which was chromatographed over silica gel (hexane/methyltert-butyl ether)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5% Palladium on carbon (0.02 g), (2S)-6-methylhept-5-en-2-ol (4.0 g, 3 mmol) and methanol (20 mL) were added to a 50 mL round-bottomed flask fitted with a magnetic stirrer. The flask was evacuated and then pressurised with 1 bar of hydrogen from a balloon. This was repeated three times then the reaction mixture was stirred for 8 hours at room temperature under hydrogen. The crude reaction mixture was filtered and the solvent removed in vacuo to yield (2S)-6-methylheptan-2-ol (3.4 g, 26 mmol, chemical yield 85%), suitable for the next stage. fitted with a magnetic stirrer The flask was evacuated The crude reaction mixture was filtered the solvent removed in vacuo