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Ketone synthesis method through alkyne hydrolysis

A hydrolysis reaction and alkyne technology, applied in the field of ketone synthesis, can solve the problems of affecting the reaction selectivity, sensitivity to light, etc., and achieve the effect of complete selectivity and high yield

Inactive Publication Date: 2016-10-19
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction also has serious defects. Silver is a noble metal and is sensitive to light, and silver itself can also catalyze the hydrolysis of alkynes, which affects the selectivity of the reaction.

Method used

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  • Ketone synthesis method through alkyne hydrolysis
  • Ketone synthesis method through alkyne hydrolysis
  • Ketone synthesis method through alkyne hydrolysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: acetophenone

[0019] Acetophenone

[0020]

[0021] Catalyst [(IPr)AuCl] (3.1 mg, 0.5 mol%), phenylacetylene (1 mmol), methanol (1 ml) and water (0.5 ml) were sequentially added to a 25 ml reactor. After the reaction mixture was reacted at 110°C for 6 hours, it was cooled to room temperature. Rotary evaporation removes solvent, then obtains pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 99%

[0022] 1HNMR (500MHz, CDCl3) δ7.99-7.94(m, 2H, ArH), 7.59-7.54(m, 1H, ArH), 7.46(t, J=7.65Hz, 2H, ArH), 2.61(s, 3H, CH3); 13C NMR (125MHz, CDCl3) δ198.03, 136.94, 132.95, 128.40, 128.13, 26.40

Embodiment 2

[0023] Embodiment 2:4-methylacetophenone

[0024] 1-p-tolylethanone

[0025]

[0026] Catalyst [(IPr)AuCl] (3.1 mg, 0.5 mol%), 4-methylphenylacetylene (1 mmol), methanol (1 ml) and water (0.5 ml) were sequentially added to a 25 ml reactor. After the reaction mixture was reacted at 110°C for 6 hours, it was cooled to room temperature. Rotary evaporation removes solvent, then obtains pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 95%

[0027] 1 HNMR (500MHz, CDCl 3 )δ7.85(d, J=8.05Hz, 2H, ArH), 7.25(d, J=8.35Hz, 2H, ArH), 2.57(s, 3H, CH 3 ),2.40(s,3H,CH 3 ); 13 C NMR (125MHz, CDCl 3 )δ197.60, 143.65, 134.49, 129.01, 128.20, 26.23, 21.37.

Embodiment 3

[0028] Embodiment 3: 3-methylacetophenone

[0029] 1-m-tolylethanone

[0030]

[0031] Catalyst [(IPr)AuCl] (3.1 mg, 0.5 mol%), 3-methylphenylacetylene (1 mmol), methanol (1 ml) and water (0.5 ml) were sequentially added to a 25 ml reactor. After the reaction mixture was reacted at 110°C for 6 hours, it was cooled to room temperature. Rotary evaporation removes solvent, then obtains pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 96%

[0032] 1H NMR (500MHz, CDCl3) δ7.78-7.73 (m, 2H, ArH), 7.40-7.33 (m, 2H, ArH), 2.59 (s, 3H, CH3), 2.41 (s, 3H, CH3); 13C NMR (125MHz, CDCl3) δ198.29, 138.22, 137.06, 133.74, 128.67, 128.32, 125.47, 26.52, 21.20.

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Abstract

The invention discloses a ketone synthesis method through alkyne hydrolysis. The method comprises the following steps: adding alkyne, a catalyst [(IPr)AuCl], a solvent methanol, and water into a reactor, carrying out reactions for several hours at a temperature of 110 to 120 DEG C, cooling to the room temperature, carrying out rotary evaporation to remove the solvent, and performing column separation to obtain target compounds. Compared with conventional ionic gold catalyst, the provided method directly uses gold chloride [(IPr)AuCl] as the catalyst, alkyne is hydrolyzed into ketone, the yield is high, the selectivity is complete, and thus the method has an important meaning for organic synthesis and environment protection.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a method for synthesizing ketones. Background technique [0002] The regioselective hydrolysis of alkynes to ketones is an important class of C–O bond-forming reactions. Because the raw material alkyne is easy to obtain, the product ketone is an important synthetic intermediate, and the atom economy of this reaction is still 100%, so it is of great significance. Using traditional methods, it can only be carried out with the participation of highly toxic mercury salts or excessive acid. In the past few years, regioselective hydrolysis of alkynes to ketones has been achieved using ionic gold as a catalyst, and the reaction exhibits high catalytic activity and excellent regioselectivity. ((a) Marion, N.; Ramon, R.S.; Nolan, S.P.J. Am. Chem. Soc. 2009, 131, 448-449. (b) Leyva, A.; Corma, A. J. Org. Chem. 2009, 74, 2067-2074 .(c) Hashmi, A.S.K.; Heng...

Claims

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Application Information

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IPC IPC(8): C07B41/06C07C45/26C07C49/78C07C49/76C07C49/84C07C49/807C07C49/80C07C49/788C07C49/04C07C49/293C07D333/22C07C255/56C07C253/30C07C205/45C07C201/12C07C225/22C07C221/00
Inventor 王娜娜马娟李峰
Owner NANJING UNIV OF SCI & TECH
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