Method for preparing benzaldehyde sulfo-acetal through benzaldehyde silicon

A technology of formaldehyde thioacetal and benzoyl silicon, applied in the field of photochemical reaction, can solve the problems of long reaction time, low yield, complicated operation, etc., and achieve the effect of short reaction time, simple and convenient operation, and less side reactions

Inactive Publication Date: 2015-04-22
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Benzaldehyde thioacetal is a commonly used aldehyde group protecting agent, which is mainly prepared by heating reaction of benzaldehyde and alkyl mercaptan at present, (L.K.Pandey, U.Pathak, R.Tank, A.Mazumder, Heterocyclic Communications, 2009, 15(3):167-172; T.W. Greene; P.G.M. Wuts, Protective groups in organic synthesis, 3 rd edition, John Wiley & Sons, Inc, 1999, 293.) This method is more complex in operation, lower in yield, longer in reaction time, and some need to add special catalysts and other defects

Method used

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  • Method for preparing benzaldehyde sulfo-acetal through benzaldehyde silicon
  • Method for preparing benzaldehyde sulfo-acetal through benzaldehyde silicon
  • Method for preparing benzaldehyde sulfo-acetal through benzaldehyde silicon

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Embodiment 1: Triethylbenzoyl silicon and butyl mercaptan prepare benzaldehyde butyl thioacetal

[0019] In a heat-resistant and pressure-resistant glass test tube, add triethylbenzoylsilyl (200mg, 0.91mmol), butylmercaptan (98mg, 1.09mmol), 35μL (4.5μmol) of pyridine and 2mL of anhydrous dichloromethane, The tube was sealed and irradiated with 250W reflected infrared light for 0.5h, the yellow color faded, and the reaction was stopped. The dichloromethane was removed under reduced pressure, and the product was separated by neutral alumina column chromatography (developing agent was n-hexane) to obtain 154mg of the product, with a yield of 63%.

Embodiment 2

[0020] Embodiment 2: Triethylbenzoyl silicon and cyclohexyl mercaptan prepare benzaldehyde cyclohexyl thioacetal

[0021] In a heat-resistant and pressure-resistant glass test tube, add triethylbenzoylsilyl (200mg, 0.91mmol), cyclohexylmercaptan (126mg, 1.09mmol), 35μL (4.5μmol) of pyridine and 2mL of anhydrous dichloromethane, The tube was sealed and irradiated with 250W reflected infrared light for 1.2h, the yellow color faded, and the reaction was stopped. The dichloromethane was removed under reduced pressure, and the product was separated by neutral alumina column chromatography (developing agent was n-hexane) to obtain 201mg of the product, with a yield of 69%.

Embodiment 3

[0022] Embodiment 3: Triethylbenzoyl silicon and tert-butyl mercaptan prepare benzaldehyde tert-butylthio acetal

[0023] In a heat-resistant and pressure-resistant glass test tube, add triethylbenzoylsilyl (200mg, 0.91mmol), tert-butylmercaptan (98mg, 1.09mmol), 35μL (4.5μmol) of pyridine and 2mL of anhydrous dichloromethane , Seal the tube, illuminate with 250W reflected infrared light for 2h, the yellow color fades, stop the reaction, remove dichloromethane under reduced pressure, and separate by neutral alumina column chromatography (developing agent is n-hexane) to obtain 176mg of product, yield 72%.

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Abstract

The invention provides a method for preparing benzaldehyde sulfo-acetal through benzaldehyde silicon, and relates to the field of preparation of sulfur compounds and silicon compounds. The benzaldehyde silicon and alkyl sulfhydryl (including primary mercaptan, secondary mercaptan and tertiary mercaptan) are used as raw materials, and benzaldehyde sulfo-acetal compounds are prepared through the photochemical reaction. The preparation method has the advantages that reagents are cheap and easy to obtain, operation is simple and convenient, the reaction time is short, and side reactions are few.

Description

technical field [0001] The invention relates to the preparation of sulfur and silicon compounds, in particular to a photochemical reaction method for preparing benzaldehyde thioacetal by using benzoyl silicon. Background technique [0002] Applying photochemistry to organic synthesis is a breakthrough in organic photochemistry, and acylsilanes (acylsilicon for short) are one of the hotspots in the field of organic photochemistry research. Acyl silicon compounds can remove silyl groups after photoexcitation to form two free radical intermediates, acyl group and silyl group. The free radical intermediates can react with other substances intermolecularly, and can also rearrange themselves. In addition, the carbonyl group can transition to the first excited singlet state or the first excited triplet state after photoexcitation, and various reactions can occur. Based on this, theoretically, a series of organic compounds can be prepared by photochemical reaction of acyl silicon. ...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C321/22C07C321/20
Inventor张彩红张国梅鲜明黄文成董川
OwnerSHANXI UNIV