1-bromo-2-methylprop-1-ene

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

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

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

Procedure: 9.23 g of 1-bromo-2-methylprop-1-ene were added dropwise to 2.5 g of magnesium turnings covered with tetrahydrofuran while heating. 7.76 g of 2-methoxyphenyl 3-methyl-2-pyridyl ketone were added while heating to reflux. After 4 hours the mixture was allowed to cool to room temperature. Saturated ammonium chloride solution was added and the resulting mixture was extracted with diethyl ether. The organic extract was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. There were obtained 5.75 g of 1-(2-methoxyphenyl)-3-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol in the form of an oil. while heating while heating to reflux the resulting mixture was extracted with diethyl ether The organic extract was dried over sodium sulphate evaporated The residue was chromatographed on silica gel for the elution

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

Procedure: 43.84 g of 1-bromo-2-methylprop-1-ene in 150 ml of tetrahydrofuran were added dropwise to 9.8 g of magnesium in 50 ml of tetrahydrofuran while heating at reflux. After 1 hour the mixture was allowed to cool to room temperature, whereupon 47.7 g of 2-methoxyphenyl 2-pyridyl ketone in 200 ml of tetrahydrofuran were added slowly. After stirring for 2 hours at room temperature 200 ml of saturated ammonium chloride were added and the mixture was extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:6) followed by ethyl acetate/petroleum ethyl (1:4) for the elution to yield 36.6 g of 1-(2-methoxyphenyl)-3-methyl-1-(2-pyridyl) -2-buten-1-ol in the form of an oil. while heating at reflux were added slowly were added the mixture was extracted with ethyl acetate The organic extract was dried over sodium sulphate evaporated The residue was chromatographed on silica gel followed by ethyl acetate/petroleum ethyl (1:4) for the elution

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

Procedure: 9.23 g of 1-bromo-2-methylprop-1-ene were added dropwise to 2.5 g of magnesium turnings covered with tetrahydrofuran while heating. 7.76 g of 2-methoxyphenyl 3-methyl-2-pyridyl ketone were added while heating to reflux. After 4 hours the mixture was allowed to cool to room temperature. Saturated ammonium chloride solution was added and the resulting mixture was extracted with diethyl ether. The organic extract was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. There were obtained 5.75 g of 1-(2-methoxyphenyl)-3-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol in the form of an oil. while heating while heating to reflux the resulting mixture was extracted with diethyl ether The organic extract was dried over sodium sulphate evaporated The residue was chromatographed on silica gel for the elution

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

Procedure: 43.84 g of 1-bromo-2-methylprop-1-ene in 150 ml of tetrahydrofuran were added dropwise to 9.8 g of magnesium in 50 ml of tetrahydrofuran while heating at reflux. After 1 hour the mixture was allowed to cool to room temperature, whereupon 47.7 g of 2-methoxyphenyl 2-pyridyl ketone in 200 ml of tetrahydrofuran were added slowly. After stirring for 2 hours at room temperature 200 ml of saturated ammonium chloride were added and the mixture was extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:6) followed by ethyl acetate/petroleum ethyl (1:4) for the elution to yield 36.6 g of 1-(2-methoxyphenyl)-3-methyl-1-(2-pyridyl)-2-buten-1-ol in the form of an oil. while heating at reflux were added slowly were added the mixture was extracted with ethyl acetate The organic extract was dried over sodium sulphate evaporated The residue was chromatographed on silica gel followed by ethyl acetate/petroleum ethyl (1:4) for the elution

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

Procedure: 43.84 g of 1-bromo-2-methylprop-1-ene in 150 ml of tetrahydrofuran were added dropwise to 9.8 g of magnesium in 50 ml of tetrahydrofuran while heating at reflux. After 1 hour the mixture was allowed to cool to room temperature, whereupon 47.7 g of 2-methoxyphenyl 2-pyridyl ketone in 200 ml of tetrahydrofuran were added slowly. After stirring for 2 hours at room temperature 200 ml of saturated ammonium chloride were added and the mixture was extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:6) followed by ethyl acetate/petroleum ethyl (1:4) for the elution to yield 36.6 g of 1-(2-methoxyphenyl)-3-methyl-1-(2-pyridyl)-2-buten-1-ol in the form of an oil. while heating at reflux were added slowly were added the mixture was extracted with ethyl acetate The organic extract was dried over sodium sulphate evaporated The residue was chromatographed on silica gel followed by ethyl acetate/petroleum ethyl (1:4) for the elution

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of magnesium (2.64 g, 110 mmol) in dry tetrahydrofuran (60 mL) was treated with a small amount of iodine and then 1-bromo-2-methylpropene (13.5 g, 100 mmol) in tetrahydrofuran (30 mL) was added in several portions. The mixture was heated under reflux for 3 min. The mixture was cooled to 25° C. and then treated with iodomethane (0.2 mL, 3.0 mmol). The reaction mixture was stirred at 25° C. for 30 min and then heated under reflux for 2 h until all the magnesium was consumed. The mixture was cooled to 25° C. then treated with a solution of tributyltin chloride (27 mL, 100 mmol) in tetrahydrofuran (30 mL). The mixture was heated under reflux for 19 h and then cooled to 25° C. The solution was extracted with diethyl ether and a saturated aqueous ammonium chloride solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford isobutenyltri-n-butyltin (31.95 g) as a crude oil. The 1H-NMR data of the crude oil indicated 58% purity of the desired isobutenyltri-n-butyltin. The mixture was heated under reflux for 3 min heated was consumed The mixture was cooled to 25° C. The mixture was heated under reflux for 19 h cooled to 25° C The solution was extracted with diethyl ether The organic layer was dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: A mixture of 10 mmoles 2-methyl-1-bromo-1-propene, 12.5 mmoles 2-methyl-3-buten-2-ol, 30 mmoles piperidine, 0.20 mmole palladium acetate and 0.40 mmole triphenylphosphine was reacted at 100° C. There was produced 61% of a mixture of nonadienols, 31% 2,6-dimethyl-6-piperidino-4-hepten-2-ol and 6% of what is believed to be 2,6-dimethyl-4-piperidino-5-hepten-2-ol. was reacted at 100° C

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

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

Procedure: A mixture of 10 mmoles 2-methyl-1-bromo-1-propene, 12.5 mmoles 2-methyl-3-buten-2-ol, 30 mmoles piperidine, 0.20 mmole palladium acetate and 0.40 mmole triphenylphosphine was reacted at 100° C. There was produced 61% of a mixture of nonadienols, 31% 2,6-dimethyl-6-piperidino-4-hepten-2-ol and 6% of what is believed to be 2,6-dimethyl-4-piperidino-5-hepten-2-ol. was reacted at 100° C

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