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Synthesis method of 5- hydroxide radical-1-indenone
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A kind of synthesis method, the technology of indanone, is applied in a kind of new synthesis field
Active Publication Date: 2013-04-10
SHANGHAI SYNTHEALL PHARM CO LTD
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It mainly solves the technical problems such as harsh reaction conditions, difficult post-processing, and difficult to obtain raw materials in the current synthesis method.
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Embodiment 1
[0022] 1. Synthesis of phenyl 3-chloropropionate
[0023]
[0024] Phenol (9.4g, 100mmol) was dissolved in 3-chloropropionyl chloride (15g, 120mmol), and the reaction mixture was stirred at 100°C for 12h under nitrogen protection, and detected by TLC until the phenol reaction was complete. The reactant was cooled to room temperature, poured into 120 mL of ice water, extracted with ethyl acetate (120 mL×3), combined the organic phases, washed with 1M NaOH, water and saturated brine, dried over anhydroussodiumsulfate, filtered to remove the desiccant, and reduced Concentrate under reduced pressure to obtain phenyl 3-chloropropionate (16.6g, yield 90%) 1 H NMR (CDCl 3 ): 3.03(t, 2H), 3.85(t, 2H), 7.09-7.12(m, 2H), 7.22-7.26(m, 1H), 7.36-7.40(m, 2H).
[0025] 2. Synthesis of 5-hydroxy-1-indanone
[0026]
[0027] Phenyl 3-chloropropionate (1.85g, 10mmol) was dissolved in trifluoromethanesulfonic acid (4.42mL, 50mmol), and the reaction mixture was placed in an oil bath w...
Embodiment 2
[0030] Synthesis of 5-Hydroxy-1-indanone
[0031]
[0032] Phenyl 3-chloropropionate (1.85g, 10mmol) was dissolved in trifluoromethanesulfonic acid (8.84mL, 100mmol), and the reaction mixture was placed in an oil bath whose temperature had reached 170°C under nitrogen protection and stirred for 2h. The reactant was cooled to room temperature, poured into 20 mL of ice water, extracted with ethyl acetate (20 mL×3), combined the organic phases, washed with saturated sodiumbicarbonate, water and saturated brine, dried over anhydroussodiumsulfate, and filtered to remove the desiccant. Concentration under reduced pressure gave 5-hydroxy-1-indanone (710 mg, yield 48%) HPLC (method: 0-60 / 6minute): Rt=3.03.
Embodiment 3
[0034] Synthesis of 5-Hydroxy-1-indanone
[0035]
[0036] Phenyl 3-chloropropionate (1.85g, 10mmol) was dissolved in trifluoromethanesulfonic acid (17.68mL, 200mmol), and the reaction mixture was placed in an oil bath whose temperature had reached 170°C under nitrogen protection and stirred for 2h. The reactant was cooled to room temperature, poured into 20 mL of ice water, extracted with ethyl acetate (20 mL×3), combined the organic phases, washed with saturated sodium bicarbonate, water and saturated brine, dried over anhydroussodium sulfate, and filtered to remove the desiccant. Concentration under reduced pressure gave 5-hydroxy-1-indanone (740 mg, yield 50%) HPLC (method: 0-60 / 6minute): Rt=3.03
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Technical field: [0001] The present invention relates to a new synthetic method of 5-hydroxyl-1-indanone. Background technique: [0002] 5-Hydroxy-1-indanone and related derivatives are widely used in medicinal chemistry and organic synthesis. The synthesis of this type of compound mainly contains the following three methods to synthesize 5 hydroxy-1-indanone at present: [0003] Method A is to take m-hydroxyphenylacetic acid as raw material, and obtain corresponding product (Hartmann, Rolf W.; Bayer, Herbert; Gruen, Gertrud; J.Med.Chem.1994,1275 -1281). The raw materials of this method are not easy to get, and more importantly, it is not easy to operate and post-process. After the reaction is often completed, the reaction bottle will be smashed to handle the reaction. [0004] The route of literature synthetic method A: [0005] [0006] Method B is to use 5-amino-1-indanone as a raw material, and convert the corresponding amino group into a hydroxyl group by Sanderm...
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