Ethanol, 2-(2-hydroxyethoxy)-, 1-(4-methylbenzenesulfonate)

Monoprotection of EthyleneglycolGeneral procedure: Oligo ethylene glycol (2 eq, 40 mmol) was dissolved intetrahydrofuran (20 mL) at 0 oC. Sodium hydroxide (1.5 eq, 30 mmol, 1.2 g) in 15 mL H2O was added drop wise to thesolution of oligo ethylene glycol. After stirring for 30 min, ptoluenesulfonylchloride (1 eq, 20 mmol, 3.8 g) was dissolvedin tetrahydrofuran (15 mL) at 0 oC. Oligoethyleneglycol was added drop wise in the solution of ptoluenesulfonylchloride. After the addition was completed, the aqueous solution was treated with HCl 10percent and extractedwith dichloromethane. The organic layer was washedwith distilled water and dried over MgSO4. After the solventwas removed, the residue was purified by column chromatography(ethyl acetate/n-hexane = 1:1 v/v) Diethylene glycol monotosylate (4a): This compoundwas obtained in 87percent yield as colourless oil; ir: 3417 (OH), 1353 and 1176 (S=O) cm-1; 1H-NMR (CDCl3): 7.72 (d, J =8.25 Hz, 3H); 7.29 (d, J = 8 Hz, 2H); 4.12 (t, J = 4.5 Hz, 2H); 3.63-3.57 (m, 3H); 3.45 (t, J = 4.75 Hz, 2H); 3.18-3.14(m, 2H); 2.38 (s, 3H). 13C-NMR (CDCl3, ): 144.9; 132.8;129.8; 128.2; 72.4; 69.3; 68.4; 61.4; 21.5.Anal. calc. forC11H16O5S1: C, 50.75; H, 6.18, S, 12.31. Found: C, 50.73; H, 6.21; S, 12.36.Compound 1-1 (166 g, 1.57 mol) was dissolved in 500 mL of tetrahydrofuran, potassium hydroxide (32 g, 571 mmol) was added in an ice bath, and then p-toluenesulfonyl chloride 1-2 (100 g, 0.52 mol) was added in batches, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into 1200 mL of water, (400 mL) and extracted twice with ethyl acetate. The extract liquid was combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure and purified by silica gel column chromatography, with an eluent (petroleum ether:ethyl acetate=1:1), to obtain the target product 1-3 (55 g, 65percent) as a colorless oil, LC-MS: m/z=261 [M+H]j00460j A solution of 2, 2’-oxybis(ethan-i-ol) 1 (5 g, 47.1 mmol) in DCM (50 mL) wascharged with silver oxide (10.3 g, 70.7 mmol), potassium iodide (1.6 g, 0.09 mmol), and tosyl chloride (9 g, 47.1 mmol) and stirred at room temperature for 12 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo resulting in a crude compound which was purified by chromatography on silica gel, eluting with 5percent methanol in DCM to give 6.9 g, 56percent yield, of the title compound as a colorless thick oil. ‘H NMR (400 MHz, CDC13): ö = 7.81 (d, J= 8.38 Hz, 2H), 7.35 (d, J= 7.94 Hz, 2H), 4.20 (t, J= 4.63 Hz, 2H), 3.65 —3.73 (m, 4H), 3.54 (d, J= 4.41 Hz, 2H), 2.45 (s, 3H), 1.94 (br. s, 1H).(1042) Step A (1043) Diethyleneglycol (1.25 g, 11.8 mmol) was dissolved in water (3.5 mL) and sodium hydroxide (0.768 g, 19.2 mmol) was added. The mixture was stirred at room temperature until a clear solution was obtained. The mixture was cooled to 0° C. and a solution of 4-toluene sulfonylchloride (2.27 g, 11.9 mmol) in tetrahydrofuran (30 mL) was dropwise added over a period of 20 minutes. After the addition was completed, the reaction mixture was stirred at 0° C. for 1 hour. The reaction mixture was diluted with ethyl acetate (150 mL) and water (40 mL). The organic phase was separated, dried over NaDiethylene glycol (3.18 g, 30 mmol) and triethylamine (TEA) (8.0 mL) were dissolved in dichloromethane (60 mL). Then, tosyl-chloride (5.70 g, 30 mmol) was added in one portion. The resulting mixture was stirred at 25 oC for 12 h. After washing with KHSO4 (1 M, 40 mL) and NaHCO3 (5percent, 40 mL), respectively and drying over Na2SO4, the crude product was obtained by evaporation and subsequently purification by column chromatography over silica gel (dichloromethane) to obtain the target product 4 as a colorless oil (3.61 g, 13.8 mmol, 46percent)To a stirred solution of diethylene glycol (compound 3A, 10.0 g, 94.2 mmol), EtTo a solution of commercially available diethyleneglycol 23 (4.0 g, 37.7 mmol) and p-toluenesulfonyl chloride (7.55 g, 39.6 mmol) stirring in anhydrousCH2Cl2 under an Ar atmosphere at 0C was slowly added Et3N (15.8mL, 113.1 mmol). After stirring overnight at rt, the reaction was diluted withCH2Cl2 and poured into a saturated aq. NaHCO3 solution. The aq. layer wasextracted three times with CH2Cl2, and the combined organic portions werewashed with brine, dried over MgSO4, and concentrated under reduced pressure.The product mixture was purified by silica gel column chromatography togive 24 (3.56 g, 36percent) as colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.83–7.76 (d, J = 8.31 Hz, 2H), 7.37–7.30 (d, J = 7.34 Hz, 2H), 4.21–4.15 (m, 2H), 3.70–3.63(m, 4H), 3.54–3.49 (m, 2H), 2.46–2.40 (s, 3H). 13C NMR (100 MHz, CDCl3): δ144.95, 129.84, 127.92, 72.46, 68.54, 61.61, 21.63.Diethylene glycol 69 (20 g, 0.188 mol) was dissolved in CHUnder the protection of nitrogen, to a 500ml three-necked flask were added 200 mL pyridine, 18.8 g BG01 (1.0eq), stirred and cooled down to 0°C. 35.5g TsCl (1.0eq) was added in batches, stirred for 1h, and then slowly warmed up to room temperature, continuing to stir for 3-4h. After the completion of the reaction, the reaction liquid was poured into the ice-cold solution of dilute hydrochloric acid, with a solid being generated, which was extracted with ethyl acetate. The ethyl acetate layer was washed once with dilute hydrochloric acid, washed with saturated sodium bicarbonate and saturated brine, and dried over anhydrous NaDiethyleneglycol (1.25 g, 11.8 mmol) was dissolved in water (3.5 mL) and sodium hydroxide (0.768 g, 19.2 mmol) was added. The mixture was stirred at room temperature until a clear solution was obtained. The mixture was cooled to 0°C and a solution of 4-toluene sulfonylchloride (2.27 g, 1 1.9 mmol) in tetrahydrofuran (30 mL) was dropwise added over a period of 20 minutes. After the addition was completed, the reaction mixture was stirred at 0°C for 1 hour. The reaction mixture was diluted with ethyl acetate (150 mL) and water (40 mL). The organic phase was separated, dried over Na

Molecular Weight:260.31
XLogP3:0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:260.07184478
Monoisotopic Mass:260.07184478
Topological Polar Surface Area:81.2
Heavy Atom Count:17
Complexity:288
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes