2-ethenoxyethanol

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

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

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

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100 ml round bottom flask fitted with a reflux condenser and a magnetic stirrer was charged with 8.8 grams (0.1 mol) of ethylene glycol monovinyl ether, 14.5 grams (0.12 mol) of allyl bromide, 4.8 grams (0-12 mol) of NaOH, 0.9 grams (3 mol %) of (n-Bu)4NBr, and 20 ml of dried toluene. The white suspension was stirred and heated at 65 ° C. for 12 hours. After cooling the reaction mixture, the resulting light yellow solution was separated from the white solids by decantation and washed with four times with 50 ml portions of water in a separatory funnel. Removal of the solvent under reduced pressure followed by vacuum distillation (b.p. 30° C./0.15 mm Hg gave the desired 1-allyloxy-2-vinyloxyethane as a colorless liquid. A 100 ml round bottom flask fitted with a reflux condenser and a magnetic stirrer After cooling the reaction mixture the resulting light yellow solution was separated from the white solids by decantation washed with four times with 50 ml portions of water in a separatory funnel Removal of the solvent under reduced pressure followed by vacuum distillation (b.p. 30° C./0.15 mm Hg

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

Procedure: To a mixture of hydoxyethyl vinyl ether (500 g) and tetra-n-butyl ammonium hydrogen sulfate (50 g), an aqueous solution of sodium hydroxide (340 g) dissolved in water ax (380 ml) was added over 30 minutes and then further stirred at room temperature for 1 hour. Further, chloromethyloxysilane (78.8 g) was added thereto and stirred at 60° C. for 2 hour. Then, ethyl acetate was added to the reaction mixture, followed by washing with water. The organic layer was extracted and dried with magnesium sulfate, and condensed at reduced pressure to distill off the solvents. The resulting liquid was purified by vacuum distillation, to obtain 530 g of the 2-glycidyloxyethyl vinyl ether (A-37) (boiling point 65° C., 532 Pa). was added over 30 minutes stirred at 60° C. for 2 hour by washing with water The organic layer was extracted dried with magnesium sulfate, and condensed at reduced pressure to distill off the solvents The resulting liquid was purified by vacuum distillation

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

Procedure: To a mixture of hydoxyethyl vinyl ether (500 g) and tetra-n-butyl ammonium hydrogen sulfate (50 g), an aqueous solution of sodium hydroxide (340 g) dissolved in water ax (380 ml) was added over 30 minutes and then further stirred at room temperature for 1 hour. Further, chloromethyloxysilane (78.8 g) was added thereto and stirred at 60° C. for 2 hour. Then, ethyl acetate was added to the reaction mixture, followed by washing with water. The organic layer was extracted and dried with magnesium sulfate, and condensed at reduced pressure to distill off the solvents. The resulting liquid was purified by vacuum distillation, to obtain 530 g of the 2-glycidyloxyethyl vinyl ether (A-37) (boiling point 65° C., 532 Pa). was added over 30 minutes stirred at 60° C. for 2 hour by washing with water The organic layer was extracted dried with magnesium sulfate, and condensed at reduced pressure to distill off the solvents The resulting liquid was purified by vacuum distillation

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Bromo-3-fluoro-5-(3-methoxypropoxy)benzene (4.0 g) was added to water (30.4 mL), and then thereto were added ethylene glycol monovinyl ether (6.8 mL), potassium carbonate (2.52 g), 1,3-bis(diphenylphosphino)propane (125 mg) and palladium acetate (34 mg), and the mixture was heated to stir at 90° C. for 22 hours. After cooling, thereto was added concentrated hydrochloric acid (7.2 mL), and the mixture was stirred at room temperature for 20 minutes. The reaction solution was extracted with ethyl acetate, washed with saturated saline, and then dried over magnesium sulfate. After concentrating under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1→2/1) to give 1-[3-fluoro-5-(3-methoxypropoxy)phenyl]ethanone [REx(19-2)] (1.03 g) as a yellow oil. the mixture was heated After cooling the mixture was stirred at room temperature for 20 minutes The reaction solution was extracted with ethyl acetate washed with saturated saline dried over magnesium sulfate After concentrating under reduced pressure the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1→2/1)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Bromo-3-fluoro-5-(3-methoxypropoxy)benzene (4.0 g) was added to water (30.4 mL), and then thereto were added ethylene glycol monovinyl ether (6.8 mL), potassium carbonate (2.52 g), 1,3-bis(diphenylphosphino)propane (125 mg) and palladium acetate (34 mg), and the mixture was heated to stir at 90° C. for 22 hours. After cooling, thereto was added concentrated hydrochloric acid (7.2 mL), and the mixture was stirred at room temperature for 20 minutes. The reaction solution was extracted with ethyl acetate, washed with saturated saline, and then dried over magnesium sulfate. After concentrating under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1→2/1) to give 1-[3-fluoro-5-(3-methoxypropoxy)phenyl]ethanone [REx(19-2)] (1.03 g) as a yellow oil. the mixture was heated After cooling the mixture was stirred at room temperature for 20 minutes The reaction solution was extracted with ethyl acetate washed with saturated saline dried over magnesium sulfate After concentrating under reduced pressure the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1→2/1)

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.81 g of ethylene glycol monovinyl ether was added to toluene (100 mL) suspension of 2.4 g of sodium hydride (55% to 72%), and 9.48 g of 2,6-dibromopyridine was added thereto and stirred overnight at 110° C. The reaction liquid was left cooled to room temperature, and water was added thereto to separate the organic layer. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. 100 mL of methanol and 576 mg of p-toluenesulfonic acid hydrate were added to the resulting residue, and stirred for 5 hours. After this was concentrated under reduced pressure, aqueous saturated sodium hydrogencarbonate solution was added to it, and extracted with ethyl acetate. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 2/1) to obtain 7.74 g of the entitled compound as a colorless oily substance. was added The reaction liquid was left cooled to room temperature to separate the organic layer This was washed with saturated saline water dried with anhydrous magnesium sulfate concentrated under reduced pressure 100 mL of methanol and 576 mg of p-toluenesulfonic acid hydrate were added to the resulting residue stirred for 5 hours After this was concentrated under reduced pressure, aqueous saturated sodium hydrogencarbonate solution was added to it extracted with ethyl acetate This was washed with saturated saline water dried with anhydrous magnesium sulfate concentrated under reduced pressure the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 2/1)

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

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Hydroxyethyl vinyl ether (0.42 mol) was added dropwise to a flask, in which sodium hydride (0.42 mol) had been dispersed in anhydrous toluene (60 ml), under a nitrogen atmosphere. After the drop addition, ethyl 7-bromoheptanoate (0.42 mol) was added dropwise. Thereafter, tetrabutylammonium iodide (2 g) was immediately added to stir the mixture at 100° C. for 3 hours. The reaction mixture was poured into water, and the resultant-organic layer was washed with water and then combined with an extract from ether. The combined layer was dried over anhydrous sodium sulfate. After the solvent was removed, the resultant residue was distilled under reduced pressure to obtain 52 g of CH2═CHOCH2CH2O(CH2)6COOC2H5 (yield: 50.7%). was added dropwise the resultant-organic layer was washed with water an extract from ether The combined layer was dried over anhydrous sodium sulfate After the solvent was removed the resultant residue was distilled under reduced pressure