2-methyl-4,5-dihydro-1,3-oxazole

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: A mixture of 4-hydroxythiophenol (2.48 g, 19.7 mmol) and 2-methyl-2-oxazoline (1.67 g, 1.69 mL, 19.7 mmol) were refluxed (neat) under argon for two hours. Upon cooling, the crude sticky solid was re-suspended in concentrated hydrochloric acid (aq) and refluxed for 12 hours. The mixture was then poured into water (20 mL) and extracted with diethyl ether (2×20 mL). The aqueous liquors were concentrated to dryness and twice re-dissolved in water and re-concentrated. Re-crystallisation of the resultant solid (ethanolidiethyl ether) gave the product as a cream solid (0.45 g, 11%); m.p. 130–31 ° C. (lit.11 128–29° C.); 1H (400 MHz, D2O) δ 3.07 (4H, br s, 2×CH2), 6.87 (2H, d, J 11.9 Hz, Ar), 7.41 (2H, d, J 11.9 Hz, Ar) were refluxed (neat) under argon for two hours Upon cooling refluxed for 12 hours extracted with diethyl ether (2×20 mL) The aqueous liquors were concentrated to dryness twice re-dissolved in water re-concentrated

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: Combine 5.0 g (0.046 mol) 4-methylphenol and 3.9 g (0.46 mol) 2-methyl-2-oxazoline under a nitrogen atmosphere and heat to 175° C. for 18 hours. After this time, cool the reaction mixture and add 50 mL of methylene chloride. Wash the organics with 3×10 mL of 10% potassium hydroxide, dry over sodium sulfate and remove the solvents to obtain the title compound. After this time, cool the reaction mixture Wash the organics with 3×10 mL of 10% potassium hydroxide dry over sodium sulfate remove the solvents

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

Procedure: 14.9 g (0.1 mol) of prenyl bromide and 8.5 g (0.1 mol) of 2-methyl-oxazoline were stirred in 50 ml of methylene chloride at 25° C. for 2 hours and the mixture was treated with 0.11 mol of a sodium butylate solution in n-butanol at 40° C. for 1 hour and worked up in the customary manner. 13.4 g (59 mmols, 59%) of 2-butoxy-2-methyl-3-(3-methyl-2-butenyl)-oxazolidine were obtained by distillation at a boiling point 78°-80° C./0.3 mm Hg.

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.5 g (0.1 mol) of 2-methyloxazoline and 14.9 g (0.1 mol) of prenyl bromide were stirred in 50 ml of n-hexane at 40° C. for 1 hour, whereupon a suspension formed, which, after adding 0.11 mol of a sodium ethylate solution in ethanol, was again stirred at 40° C. for 1 hour. The solution was filtered, the filtrate was concentrated on a rotary evaporator and the residue was distilled using an oil pump. 12.3 g (0.062 mol, 62%) of 2-ethoxy-2-methyl-3-(3-methyl-2-butenyl)-oxazolidine were isolated at a boiling point 67° C./0.1 mm Hg. formed The solution was filtered the filtrate was concentrated on a rotary evaporator the residue was distilled

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.5 g (0.1 mol) of 2-methyloxazoline and 14.9 g (0.1 mol) of prenyl bromide were stirred in 50 ml of n-hexane at 40° C. for 1 hour, whereupon a suspension formed, which, after adding 0.11 mol of a sodium ethylate solution in ethanol, was again stirred at 40° C. for 1 hour. The solution was filtered, the filtrate was concentrated on a rotary evaporator and the residue was distilled using an oil pump. 12.3 g (0.062 mol, 62%) of 2-ethoxy-2-methyl-3-(3-methyl-2-butenyl)-oxazolidine were isolated at a boiling point 67° C./0.1 mm Hg. formed The solution was filtered the filtrate was concentrated on a rotary evaporator the residue was distilled

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

Procedure: 8.5 g (0.1 mol) of 2-methyloxazoline and 14.9 g (0.1 mol) of 3-methyl-2-butenyl bromide were stirred in 50 ml of acetonitrile at 20° to 25° C. for 2 hours and, after adding 20 ml of a 5 N sodium methylate solution, the mixture was stirred at room temperature for a further 3 hours. The solution was filtered and, after stripping off the solvent, the residue was distilled. 15.6 g (84 mmols, 84%) of 2-methoxy-2-methyl-3-(3-methyl-2-butenyl)-oxazolidine of boiling point 96°-99° C./20 mm Hg were obtained. The solution was filtered the residue was distilled

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

Procedure: 8.5 g (0.1 mol) of 2-methyloxazoline and 14.9 g (0.1 mol) of 3-methyl-2-butenyl bromide (prenyl bromide) were stirred at 20°-25° C. for 2 hours, crystalline, hygroscopic 2-methyl-3-(3-methyl-2-butenyl)-2-oxazolinium bromide being formed in an exothermic reaction.

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

Procedure: 8.5 g (0.1 mol) of 2-methyloxazoline and 14.9 g (0.1 mol) of 3-methyl-2-butenyl bromide (prenyl bromide) were stirred at 20°-25° C. for 2 hours, crystalline, hygroscopic 2-methyl-3-(3-methyl-2-butenyl)-2-oxazolinium bromide being formed in an exothermic reaction.