四甘醇单烯丙基醚

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-{2-[2-(2-allyloxy-ethoxy)-ethoxy]-ethoxy}-ethanol (9) (3.6 g, 15 mmol), succinic anhydride (1.8 g, 18 mmol), pyridine (1.22 mL, 15 mmol), dimethylaminopyridine (183 mg, 10 mol %), and dry toluene (5 mL) were charged into a screw cap culture tube. The mixture was stirred at 80° C. for 10 hours. Next, the reaction was stopped by adding 10% HCl (6 mL) and the reaction mixture was extracted with CH2Cl2 (3×10 mL). An organic layer was collected and dried on MgSO4. AMBERLITE™ resin IR-120 (+) (2 g) was added and stirred to perform ion exchange. The resin was filtered off and the filtrate was concentrated to obtain yellow oil (5.2 g, 92%). The compound was used without further purification. The NMR analysis result of the compound is as follows. cap culture tube the reaction mixture was extracted with CH2Cl2 (3×10 mL) An organic layer was collected dried on MgSO4 was added stirred The resin was filtered off the filtrate was concentrated

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-{2-[2-(2-allyloxy-ethoxy)-ethoxy]-ethoxy}-ethanol (9) (3.6 g, 15 mmol), succinic anhydride (1.8 g, 18 mmol), pyridine (1.22 mL, 15 mmol), dimethylaminopyridine (183 mg, 10 mol %), and dry toluene (5 mL) were charged into a screw cap culture tube. The mixture was stirred at 80° C. for 10 hours. Next, the reaction was stopped by adding 10% HCl (6 mL) and the reaction mixture was extracted with CH2Cl2 (3×10 mL). An organic layer was collected and dried on MgSO4. AMBERLITE™ resin IR-120 (+) (2 g) was added and stirred to perform ion exchange. The resin was filtered off and the filtrate was concentrated to obtain yellow oil (5.2 g, 92%). The compound was used without further purification. The NMR analysis result of the compound is as follows. cap culture tube the reaction mixture was extracted with CH2Cl2 (3×10 mL) An organic layer was collected dried on MgSO4 was added stirred The resin was filtered off the filtrate was concentrated

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-{2-[2-(2-allyloxy-ethoxy)-ethoxy]-ethoxy}-ethanol (9) (3.6 g, 15 mmol), succinic anhydride (1.8 g, 18 mmol), pyridine (1.22 mL, 15 mmol), dimethylaminopyridine (183 mg, 10 mol %), and dry toluene (5 mL) were charged into a screw cap culture tube. The mixture was stirred at 80° C. for 10 hours. Next, the reaction was stopped by adding 10% HCl (6 mL) and the reaction mixture was extracted with CH2Cl2 (3×10 mL). An organic layer was collected and dried on MgSO4. AMBERLITE™ resin IR-120 (+) (2 g) was added and stirred to perform ion exchange. The resin was filtered off and the filtrate was concentrated to obtain yellow oil (5.2 g, 92%). The compound was used without further purification. The NMR analysis result of the compound is as follows. cap culture tube the reaction mixture was extracted with CH2Cl2 (3×10 mL) An organic layer was collected dried on MgSO4 was added stirred The resin was filtered off the filtrate was concentrated

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Under nitrogen atmosphere, NaH (1.2 g, 50 mmol) was charged into a flask, and then dry THF (15 mL) was added thereto and stirred at 0° C. for 15 minutes. Tetraethyleneglycol (10.7 g, 55 mmol) was added to the NaH mixture at 0° C. The mixture was stirred at room temperature for 1 hour. Next, the mixture was diluted with water (20 mL) and an organic material was extracted with methylene chloride (3×10 mL). The resulting organic layer was collected, dried on MgSO4 and concentrated to obtain a crude product as yellow liquid. The crude product was purified with a column chromatography (Hex:EA=1:2 (10% MeOH)) to obtain the target product (3.8 g, 32%) in a colorless oily phase. The NMR analysis result of the obtained product is as follows. The mixture was stirred at room temperature for 1 hour an organic material was extracted with methylene chloride (3×10 mL) The resulting organic layer was collected dried on MgSO4 concentrated to obtain a crude product as yellow liquid The crude product was purified with a column chromatography (Hex:EA=1:2 (10% MeOH))

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Under nitrogen atmosphere, NaH (1.2 g, 50 mmol) was charged into a flask, and then dry THF (15 mL) was added thereto and stirred at 0° C. for 15 minutes. Tetraethyleneglycol (10.7 g, 55 mmol) was added to the NaH mixture at 0° C. The mixture was stirred at room temperature for 1 hour. Next, the mixture was diluted with water (20 mL) and an organic material was extracted with methylene chloride (3×10 mL). The resulting organic layer was collected, dried on MgSO4 and concentrated to obtain a crude product as yellow liquid. The crude product was purified with a column chromatography (Hex:EA=1:2 (10% MeOH)) to obtain the target product (3.8 g, 32%) in a colorless oily phase. The NMR analysis result of the obtained product is as follows. The mixture was stirred at room temperature for 1 hour an organic material was extracted with methylene chloride (3×10 mL) The resulting organic layer was collected dried on MgSO4 concentrated to obtain a crude product as yellow liquid The crude product was purified with a column chromatography (Hex:EA=1:2 (10% MeOH))

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Under nitrogen atmosphere, NaH (1.2 g, 50 mmol) was charged into a flask, and then dry THF (15 mL) was added thereto and stirred at 0° C. for 15 minutes. Tetraethyleneglycol (10.7 g, 55 mmol) was added to the NaH mixture at 0° C. The mixture was stirred at room temperature for 1 hour. Next, the mixture was diluted with water (20 mL) and an organic material was extracted with methylene chloride (3×10 mL). The resulting organic layer was collected, dried on MgSO4 and concentrated to obtain a crude product as yellow liquid. The crude product was purified with a column chromatography (Hex:EA=1:2 (10% MeOH)) to obtain the target product (3.8 g, 32%) in a colorless oily phase. The NMR analysis result of the obtained product is as follows. The mixture was stirred at room temperature for 1 hour an organic material was extracted with methylene chloride (3×10 mL) The resulting organic layer was collected dried on MgSO4 concentrated to obtain a crude product as yellow liquid The crude product was purified with a column chromatography (Hex:EA=1:2 (10% MeOH))

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 11-allyloxy-3,6,9-trioxaundecanol (83, 2.33 g, 9.94 mmol) in dry THF (40 mL), sodium hydride (0.95 g, 39.8 mmol) is added in several portions under an argon atmosphere. The mixture is stirred for 30 min. A solution of the iodo derivative 45 (3.0 g, 8.28 mmol) in dry THF (10 mL) is added dropwise, and the mixture stirred for 15 h. The reaction is quenched by adding 2 mL of water, and 70% of the amount of THF is evaporated in vacuo. To dilute the mixture, 70 mL of water are added, and the solution extracted with 5 times 50 mL ethyl acetate. The combined organic extracts are dried over MgSO4 and concentrated in vacuo. The yellow oil obtained is purified by flash column chromatography (gradient petrol ether/ethyl acetate 10:1 to 5:1) to give the title product 84 as a pale yellow oil (1.96 g, 4.2 mmol, 51%). the mixture stirred for 15 h The reaction is quenched by adding 2 mL of water, and 70% of the amount of THF is evaporated in vacuo To dilute the mixture, 70 mL of water are added the solution extracted with 5 times 50 mL ethyl acetate The combined organic extracts are dried over MgSO4 concentrated in vacuo The yellow oil obtained is purified by flash column chromatography (gradient petrol ether/ethyl acetate 10:1 to 5:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To an anhydrous solution of potassium tert-butoxide (2.3 g, 19.5 mmol) in THF (500 mL), tetraethylene glycol (7.18 g, 37.0 mmol) is added at room temperature. The resulting mixture is stirred for 30 min, and a solution of allyl iodide (3.31 g, 19.7 mmol) in dry THF (60 mL) is added dropwise over 1 h. The reaction mixture is stirred for 30 h and filtered through a silica plug (10 g) using ethyl acetate (800 mL) to elute all product. After evaporation of the solvent in vacuo, the product is purified by column chromatography using a solvent gradient petrol ether/ethyl acetate 10:1 to ethyl acetate 100% yielding a colourless oil (2.41 g, 10.3 mmol, 27%). The reaction mixture is stirred for 30 h filtered through a silica plug (10 g) to elute all product After evaporation of the solvent in vacuo the product is purified by column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2.3 g (19.5 mmol) Potassium tert-butoxide is dissolved in 500 mL dry THF, and 7.18 g (37 mmol) tetraethylene glycol is added dropwise. After stirring for 30 min, a solution of 3.31 g (19.7 mmol) allyl iodide in 60 mL dry THF is added over 1 h, and stirring is continued for 24 h. The crude mixture is filtered over silica gel and the solvent removed in vacuo. The product is purified by silica gel chromatography (gradient: petrol ether/ethyl acetate 10:1→ethyl acetate), yielding 2.41 g 22 (10.3 mmol, 27%) as a colorless liquid. stirring is continued for 24 h The crude mixture is filtered over silica gel the solvent removed in vacuo The product is purified by silica gel chromatography (gradient: petrol ether/ethyl acetate 10:1→ethyl acetate)