pent-3-en-2-ol

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

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

Procedure: A 1-liter flask was charged with 43.9 g (0.51 mol) of 3-penten-2-ol, 51.6 g (0.51 mol) of triethylamine and 300 ml of dichloromethane, and the mixture was cooled down to 0° C. While stirring the mixture at 0° C., 52.3 g (0.50 mol) of methacryloyl chloride were added dropwise over 1 hour, and the mixture was stirred additionally for 5 hours at room temperature. Solids were separated by filtration from the resultant reaction mixture, and the filtrate was washed 3 times with water and then distilled in the presence of 5 g of p-methoxyphenol to obtain 42.4 g of 1-methyl-2-butenyl methacrylate. the mixture was stirred additionally for 5 hours at room temperature Solids were separated by filtration from the resultant reaction mixture the filtrate was washed 3 times with water distilled in the presence of 5 g of p-methoxyphenol

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

Procedure: A mixture of 0.6 g of 5% palladium on carbon, 44.1 g (0.15 moles of the pent-3-en-2-ol) of the above pentenol/pentanol mixture and 50 ml of ethanol was hydrogenated at 25°-45° C and 35-52 psi until hydrogen uptake ceased. The mixture was filtered to remove the catalyst and the solvent was removed from the filtrate by distillation. The residual oil was fractionally distilled to yield 5-(2,2,3-trimethylcyclopent-3-en-1-yl)-pentan-2-ol 30.1 g (77.7% yield); bp 105-108° C (1.5 mm); mol wt. 196 (ms); ir, 3350 (s, broad), 3040 and 797 cm-1 ; nmr, 0.5δ, 0.8, 0.9 and 1.0 (6H, 4s, geminal dimethyl groups of various diastereomers in the mixture), 1.2 (3H, d, J~6 Hz, carbinol methyl), 1.3-1.5 (7H, broad complex), 1.6 (3H, broad s, olefinic methyl), 1.7-2.4 (3H, broad complex containing 1H exchangeable with D2O), 3.8 (1H, broad multiplet, carbinyl H), 5.2 (1H, broad multiplet, olefinic H). was hydrogenated at 25°-45° C The mixture was filtered to remove the catalyst the solvent was removed from the filtrate by distillation The residual oil was fractionally distilled

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

Procedure: 32 mg 3-penten-2-ol (0.38 mmol,) in 1 ml dry dichloromethane were treated at 0° C. with 62 mg 1,1′-carbonyl-diimidazole. The mixture was stirred at 0° C. for 2 hrs. 80 mg 2-phenyl-3H-imidazo[4,5-b]pyridin-6-ylamine (0.38 mmol,) in 0.5 ml N-methylpyrrolidone (NMP) were added and the mixture stirred over night at room temperature. 1 ml water was added, the precipitate filtered, and the filter residue washed thoroughly with water and ether and further purified by chromatography. the mixture stirred over night at room temperature the precipitate filtered the filter residue washed thoroughly with water and ether further purified by chromatography

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

Procedure: A 1-liter flask was charged with 43.9 g (0.51 mol) of 3-penten-2-ol, 51.6 g (0.51 mol) of triethylamine and 300 ml of dichloromethane, and the mixture was cooled down to 0° C. While stirring the mixture at 0° C., 52.3 g (0.50 mol) of methacryloyl chloride were added dropwise over 1 hour, and the mixture was stirred additionally for 5 hours at room temperature. Solids were separated by filtration from the resultant reaction mixture, and the filtrate was washed 3 times with water and then distilled in the presence of 5 g of p-methoxyphenol to obtain 42.4 g of 1-methyl-2-butenyl methacrylate. the mixture was stirred additionally for 5 hours at room temperature Solids were separated by filtration from the resultant reaction mixture the filtrate was washed 3 times with water distilled in the presence of 5 g of p-methoxyphenol

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 0.6 g of 5% palladium on carbon, 44.1 g (0.15 moles of the pent-3-en-2-ol) of the above pentenol/pentanol mixture and 50 ml of ethanol was hydrogenated at 25°-45° C and 35-52 psi until hydrogen uptake ceased. The mixture was filtered to remove the catalyst and the solvent was removed from the filtrate by distillation. The residual oil was fractionally distilled to yield 5-(2,2,3-trimethylcyclopent-3-en-1-yl)-pentan-2-ol 30.1 g (77.7% yield); bp 105-108° C (1.5 mm); mol wt. 196 (ms); ir, 3350 (s, broad), 3040 and 797 cm-1 ; nmr, 0.5δ, 0.8, 0.9 and 1.0 (6H, 4s, geminal dimethyl groups of various diastereomers in the mixture), 1.2 (3H, d, J~6 Hz, carbinol methyl), 1.3-1.5 (7H, broad complex), 1.6 (3H, broad s, olefinic methyl), 1.7-2.4 (3H, broad complex containing 1H exchangeable with D2O), 3.8 (1H, broad multiplet, carbinyl H), 5.2 (1H, broad multiplet, olefinic H). was hydrogenated at 25°-45° C The mixture was filtered to remove the catalyst the solvent was removed from the filtrate by distillation The residual oil was fractionally distilled

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

Procedure: 32 mg 3-penten-2-ol (0.38 mmol,) in 1 ml dry dichloromethane were treated at 0° C. with 62 mg 1,1′-carbonyl-diimidazole. The mixture was stirred at 0° C. for 2 hrs. 80 mg 2-phenyl-3H-imidazo[4,5-b]pyridin-6-ylamine (0.38 mmol,) in 0.5 ml N-methylpyrrolidone (NMP) were added and the mixture stirred over night at room temperature. 1 ml water was added, the precipitate filtered, and the filter residue washed thoroughly with water and ether and further purified by chromatography. the mixture stirred over night at room temperature the precipitate filtered the filter residue washed thoroughly with water and ether further purified by chromatography

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

Procedure: A 1-liter flask was charged with 43.9 g (0.51 mol) of 3-penten-2-ol, 51.6 g (0.51 mol) of triethylamine and 300 ml of dichloromethane, and the mixture was cooled down to 0° C. While stirring the mixture at 0° C., 52.3 g (0.50 mol) of methacryloyl chloride were added dropwise over 1 hour, and the mixture was stirred additionally for 5 hours at room temperature. Solids were separated by filtration from the resultant reaction mixture, and the filtrate was washed 3 times with water and then distilled in the presence of 5 g of p-methoxyphenol to obtain 42.4 g of 1-methyl-2-butenyl methacrylate. the mixture was stirred additionally for 5 hours at room temperature Solids were separated by filtration from the resultant reaction mixture the filtrate was washed 3 times with water distilled in the presence of 5 g of p-methoxyphenol

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