2-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethanol

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

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 10 mL Schlenk tube containing potassium tert-butoxide (125 mg, 1 mmol, 0,5 eq.) under nitrogen atmosphere, was added freshly distilled 2,2-dimethyl-3-(2-hydroxyethyl)-oxazolidine (1,4 mL, 10 mmol, d 1,035, 5 eq.) before heating at 75° C. until complete dissolution. To the solution was added slowly 2-(4-propyl-heptyl)-oxirane (0,43 mL, 2 mmol, d 0,856) over 1 h at 75° C. The reaction was stirred at 75° C. After 6 h, the reaction was cooled to room temperature before adding diethyl ether (40 mL). The organic phase was extracted with aqueous hydrochloric acid (1 M, 3×12 mL). Then, a solution of aqueous sodium hydroxide (25%) was added to bring the mixture to pH 14 before extracting it with diethyl ether (4×16 mL). The combined organic phases were dried over sodium sulfate and concentrated to afford the title compound (515 mg, 90% yield). 1H NMR (CDCl3, 400 MHz) d?(ppm): 3,83-3,74 (m, H); 3,67 (t, J=5,2 Hz, 2H); 3,67-3,56 (m, 2H); 3,52 (dd, J=2,7 Hz, J=9,9 Hz, H); 3,30 (dd, J=8,2 Hz, J=9,9 Hz, H); 3,05-2,96 (m, 2H+2H); 1,50-1,15 (m, 15H); 0,87 (t, J=7,0 Hz, 6H). 13C NMR (CDCl3, 129,9 MHz) d?(ppm): 75,9; 70,3; 70,2; 60,9; 51,1; 48,9; 36,9; 36,0 (2C); 33,7; 33,6; 22,7; 19,8 (2C); 14,5 (2C). the reaction was cooled to room temperature The organic phase was extracted with aqueous hydrochloric acid (1 M, 3×12 mL) Then, a solution of aqueous sodium hydroxide (25%) was added before extracting it with diethyl ether (4×16 mL) The combined organic phases were dried over sodium sulfate concentrated

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

Procedure: To a 100 mL flask containing diethanolamine (19,2 mL, 200 mmol) was added acetone (29,4 mL, 400 mmol, 2 eq.) and potassium carbonate (pulverised and dried at 160° C., 27,6 g, 200 mmol, 1 eq.). The reaction was stirred at room temperature for one day. The mixture was filtered through a sinter funnel (no. 3) and the collected solid was washed with acetone. The filtrate and the washes were combined and the solvent evaporated. The 1H NMR indicated a conversion of 85%. Distillation at 125-132 ° C./20 mmHg of the crude reaction gave the title product (20,89 g, 72% yield) as a colourless oil. 1H NMR (CDCl3, 400 MHz) d?(ppm): 3,93 (t, J=6,6 Hz, 2H); 3,62 (t, J=5,3 Hz, 2H); 2,96 (t, J=6,6 Hz, 2H); 2,65 (t, J=5,3 Hz, 2H); 1,23 (s, 6H). 13C NMR (CDCl3, 129,9 MHz) d??(ppm): 94,2; 63,5; 59,3; 50,8; 49,1; 23,3 (2C). The mixture was filtered through a sinter funnel (no 3) and the collected solid was washed with acetone the solvent evaporated Distillation at 125-132 ° C./20 mmHg of the crude reaction

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

Procedure: Part (A) of Example I is a process for making MEHEOX, i.e., 2-ethyl-3-(2-hydroxyethyl)-2-methyl-oxazolidine by reaction of diethanolamine with methyl ethyl ketone. Replacement of the latter ketone with acetone in molarly corresponding amount yields 3-(2-hydroxyethyl)-2,2-dimethyl-oxazolidine, herein referred to by the acronym DMHEOX, i.e., dimethyl-hydroxyethyl-oxazolidine. Replacement of the ketone with cyclopentanone or cyclohexanone yields 3-(2-hydroxyethyl)-2,2-tetramethylene- or 3-(2-hydroxyethyl)-2,2-pentamethylene-oxazolidine.

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

Procedure: Part (A) of Example I is a process for making MEHEOX, i.e., 2-ethyl-3-(2-hydroxyethyl)-2-methyl-oxazolidine by reaction of diethanolamine with methyl ethyl ketone. Replacement of the latter ketone with acetone in molarly corresponding amount yields 3-(2-hydroxyethyl)-2,2-dimethyl-oxazolidine, herein referred to by the acronym DMHEOX, i.e., dimethyl-hydroxyethyloxazolidine. Replacement of the ketone with cyclopentanone or cyclohexanone yields 3-(2-hydroxyethyl)-2,2-tetramethylene- or 3-(2-hydroxyethyl)-2,2-pentamethylene-oxazolidine.

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 10 mL Schlenk tube containing potassium tert-butoxide (125 mg, 1 mmol, 0,5 eq.) under nitrogen atmosphere, was added freshly distilled 2,2-dimethyl-3-(2-hydroxyethyl)-oxazolidine (1,4 mL, 10 mmol, d 1,035, 5 eq.) before heating at 75° C. until complete dissolution. To the solution was added slowly 2-(4-propyl-heptyl)-oxirane (0,43 mL, 2 mmol, d 0,856) over 1 h at 75° C. The reaction was stirred at 75° C. After 6 h, the reaction was cooled to room temperature before adding diethyl ether (40 mL). The organic phase was extracted with aqueous hydrochloric acid (1 M, 3×12 mL). Then, a solution of aqueous sodium hydroxide (25%) was added to bring the mixture to pH 14 before extracting it with diethyl ether (4×16 mL). The combined organic phases were dried over sodium sulfate and concentrated to afford the title compound (515 mg, 90% yield). 1H NMR (CDCl3, 400 MHz) d?(ppm): 3,83-3,74 (m, H); 3,67 (t, J=5,2 Hz, 2H); 3,67-3,56 (m, 2H); 3,52 (dd, J=2,7 Hz, J=9,9 Hz, H); 3,30 (dd, J=8,2 Hz, J=9,9 Hz, H); 3,05-2,96 (m, 2H+2H); 1,50-1,15 (m, 15H); 0,87 (t, J=7,0 Hz, 6H). 13C NMR (CDCl3, 129,9 MHz) d?(ppm): 75,9; 70,3; 70,2; 60,9; 51,1; 48,9; 36,9; 36,0 (2C); 33,7; 33,6; 22,7; 19,8 (2C); 14,5 (2C). the reaction was cooled to room temperature The organic phase was extracted with aqueous hydrochloric acid (1 M, 3×12 mL) Then, a solution of aqueous sodium hydroxide (25%) was added before extracting it with diethyl ether (4×16 mL) The combined organic phases were dried over sodium sulfate concentrated

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

Procedure: To a 100 mL flask containing diethanolamine (19,2 mL, 200 mmol) was added acetone (29,4 mL, 400 mmol, 2 eq.) and potassium carbonate (pulverised and dried at 160° C., 27,6 g, 200 mmol, 1 eq.). The reaction was stirred at room temperature for one day. The mixture was filtered through a sinter funnel (no. 3) and the collected solid was washed with acetone. The filtrate and the washes were combined and the solvent evaporated. The 1H NMR indicated a conversion of 85%. Distillation at 125-132 ° C./20 mmHg of the crude reaction gave the title product (20,89 g, 72% yield) as a colourless oil. 1H NMR (CDCl3, 400 MHz) d?(ppm): 3,93 (t, J=6,6 Hz, 2H); 3,62 (t, J=5,3 Hz, 2H); 2,96 (t, J=6,6 Hz, 2H); 2,65 (t, J=5,3 Hz, 2H); 1,23 (s, 6H). 13C NMR (CDCl3, 129,9 MHz) d??(ppm): 94,2; 63,5; 59,3; 50,8; 49,1; 23,3 (2C). The mixture was filtered through a sinter funnel (no 3) and the collected solid was washed with acetone the solvent evaporated Distillation at 125-132 ° C./20 mmHg of the crude reaction

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

Procedure: Part (A) of Example I is a process for making MEHEOX, i.e., 2-ethyl-3-(2-hydroxyethyl)-2-methyl-oxazolidine by reaction of diethanolamine with methyl ethyl ketone. Replacement of the latter ketone with acetone in molarly corresponding amount yields 3-(2-hydroxyethyl)-2,2-dimethyl-oxazolidine, herein referred to by the acronym DMHEOX, i.e., dimethyl-hydroxyethyl-oxazolidine. Replacement of the ketone with cyclopentanone or cyclohexanone yields 3-(2-hydroxyethyl)-2,2-tetramethylene- or 3-(2-hydroxyethyl)-2,2-pentamethylene-oxazolidine.

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

Procedure: Part (A) of Example I is a process for making MEHEOX, i.e., 2-ethyl-3-(2-hydroxyethyl)-2-methyl-oxazolidine by reaction of diethanolamine with methyl ethyl ketone. Replacement of the latter ketone with acetone in molarly corresponding amount yields 3-(2-hydroxyethyl)-2,2-dimethyl-oxazolidine, herein referred to by the acronym DMHEOX, i.e., dimethyl-hydroxyethyl-oxazolidine. Replacement of the ketone with cyclopentanone or cyclohexanone yields 3-(2-hydroxyethyl)-2,2-tetramethylene- or 3-(2-hydroxyethyl)-2,2-pentamethylene-oxazolidine.

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

Conditions: temp:37.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 526 g (5.0 moles) of diethanolamine, 581 g (10 moles) of acetone and 690 g (5.0 moles) of anhydrous potassium carbonate are allowed to stir for 20 hours. During the first two hours the solution temperature gradually increases to a maximum of 37° C. The mixture is filtered and the collected solid is washed with 500 ml of acetone. The filtrate and wash are combined, the solvent distilled off under reduced pressure, and the residue distilled under reduced pressure. There is obtained 543 g (75%) of a colorless liquid, b.p. 89°-92°/8 mm, nD26 1.4614, neutralization equivalent 144.5 (calculated 145.2). The mixture is filtered the collected solid is washed with 500 ml of acetone The filtrate and wash the solvent distilled off under reduced pressure the residue distilled under reduced pressure

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

Procedure: Part (A) of Example I is a process for making MEHEOX, i.e., 2-ethyl-3-(2-hydroxyethyl)-2-methyloxazolidine by reaction of diethanolamine with methyl ethyl ketone. Replacement of the latter ketone with acetone in molarly corresponding amount yields 3-(2-hydroxyethyl)-2,2-dimethyl-oxazolidine, herein referred to by the acronym DMHEOX, i.e., dimethyl-hydroxyethyloxazolidine. Replacement of the ketone with cyclopentanone or cyclohexanone yields 3-(2-hydroxyethyl)-2,2-tetramethylene- or 3-(2-hydroxyethyl)-2,2-pentamethylene-oxazolidine.