1-BENZYLOXY-2-PROPANOL

11 g of benzyl alcohol (0.1 mol) and 11.4 g of potassium t-butoxide (first catalyst, 0.1 mol) were added to 150 mL of anhydrous THF at 0 ° C, and stirred for 30 min.The first mixture was obtained. Drop the ring into the first mixture at 0 ° COxypropane is subjected to a ring opening reaction and stirred for 24 hours, wherein benzyl alcohol, The molar ratio of propylene oxide to the first catalyst was 1:1:1. Adjusting the pH of the above ring-opening reaction system to 7 with a 30 wtpercent aqueous solution of dilute acetic acid.After THF was spin-dried, 300 mL of ethyl acetate was added for extraction.The organic phase was washed 3 times with 100 mL of purified water.Then dried with 25 g of anhydrous sodium sulfate for 3 h, after filtering the desiccant, The organic phase was dried to ethyl acetate: n-heptane = 1:5 column chromatographyThere was obtained 13.8 g of a colorless oil (ring-opening product) in a yield of 90percent by weight.The 1, 2-propanediol (5g, 65.7mmol) and NaH (3.29g, 82 . 0mmol) dissolved in N, N-dimethylformamide (70 ml) in. In 0 °C add benzyl bromide (7.82 ml, 65 . 7mmol), then stirring 2 hours. After the reaction is completed, water and ethyl acetate extraction. Organic layer is dried with anhydrous sodium sulfate, filtered and concentrated. Purification of the residue column chromatographying. Generating title compound (4.45g, 41percent).1, 2-propanediol (5 g, 65.7 mmol) and NaH (3.29 g, 82.0 mmol) were dissolved in N, N-dimethylformamide (70 mL). benzyl bromide (7.82 mL, 65.7 mmol) was added at 0° C., followed by stirring for 2 hr. After reaction was finished, extraction was performed with water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by a column chromatography. The title compound (4.45 g, 41percent) was produced. 10 g of ring-opening product, 2.85 g of vinyl acetate, 200 mL of water and 10 mL of DMSO were mixed and mixed to obtain a second mixture.The pH of the above second mixture was adjusted to 6 using PBS buffer (main components are Na2HPO4, KH2PO4, NaCl, and KCl), and then 5 mL of esterase (horse liver esterase) crude enzyme was added to the above second mixture. Aqueous solution, And stirring at 30 ° C for 7 h, wherein the concentration of esterase was 1 U / mL.The progress of the reaction was detected by HPLC. After the reaction was completed, 50 mL of anhydrous B was added.The alcohol terminates the reaction. The reaction system was extracted 3 times with 100 mL of ethyl acetate.The organic phases were combined and the organic phase was washed with 50 mL of brine.It was dried over 10 g of anhydrous sodium sulfate for 30 min. Sodium sulfate is removed by filtration, The organic phase was dried to give 9.57 g of a pale yellow oil (ester-transfer product).The yield was 85 wtpercent and the molar ratio of the two products was 1:0.97.11.0 g of an oily mixture (transesterification product) was added to 100 mL of anhydrous dichloromethane to obtain a mixed liquid. 6.00 g of TsCl (0.03 mol) and 5 g of diisopropylethylamine (0.039 mol) were added to the above mixture under nitrogen atmosphere.The first sulfonylation reaction is carried out. At room temperature, the reaction was carried out for 8 h.The reaction was confirmed to be complete by HPLC. Add 200 mL to the above reaction systemDichloromethane, washed twice with 50 mL of 10 wtpercent aqueous citric acid solution.It was washed once with 50 mL of purified water. Then, the organic phase was dried over 20 g of anhydrous sodium sulfate for 30 min, and after removing sodium sulfate by filtration, the organic phase was dried to give 12.72 g of a mixture (first sulfonylated product) in a yield of 80percent by weight. The molar ratio of the two products was 1:1.

1-Benzyloxy-2-propanol is an intermediate used in the synthetic preparation of glucokinase activators for the treatment of diabetes.

Molecular Weight:166.22
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:166.099379685
Monoisotopic Mass:166.099379685
Topological Polar Surface Area:29.5
Heavy Atom Count:12
Complexity:108
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes