124391-75-9Relevant academic research and scientific papers
Novel and efficient catalytic route for the syntheses of tetrahydrofurans useful in the preparation of neonicotinoid insecticides
Potluri, Srinagesh Kumar,Ramulu, A. Raghu,Pardhasaradhi
, p. 971 - 978 (2005)
Neonicotinoids are good alternatives to the widely used organophosphate insecticides (OP) and have gained enormous importance because of their low toxicity in vertebrates. An environmentally benign route for the synthesis of 3-(hydroxy-methyl)tetrahydrofuran useful in the preparation of a neonicotinoid insecticide viz. MTI-446 is described. Principles of green chemistry such as hydroformylation, single-pot transketalization, and intramolecular cyclocondensation through catalytic reactions were adopted. The process reported here is superior to the existing methods with respect to lower salt formation and higher atom economy, and it was extended to the preparation of a novel intermediate, 3,3-bis(hydroxymethyl)tetrahydrofuran, conceived to be useful in the preparation of new insecticides.
STRUCTURE AND FORMATION OF C4H7O(1+) IONS RESULTING FROM ELECTRON IMPACT INDUCED DECOMPOSITION OF CYCLIC PRECURSORS
Stolze, Rainer,Budzikiewicz, Herbert
, p. 781 - 787 (1981)
Possible structures and modes of formation of C4H7O(1+) ions formed by electron impact induced decomposition of tetrahydrofuran and tetrahydropyran derivates are discussed in view of labelling results and MIKE, CA, and T data.Limitations of these techniques are pointed out.
3-(5-METHOXY-1-OXOISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE DERIVATIVES AND USES THEREOF
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Page/Page column 328-329, (2021/06/26)
The present disclosure relates to compounds of formula (I') and pharmaceutical compositions and their use in reducing Widely Interspaced Zinc Finger Motifs (WIZ) expression levels, or inducing fetal hemoglobin (HbF) expression, and in the treatment of inherited blood disorders (e.g., hemoglobinopathies, e.g., beta-hemoglobinopathies), such as sickle cell disease and beta-thalassemia.
Production technology for 3-hydroxymethyltetrahydrofuran
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Paragraph 0033; 0034; 0037; 0043, (2018/10/19)
The invention discloses a production technology for 3-hydroxymethyltetrahydrofuran, and belongs to the field of pesticide intermediate synthetic processes. The production technology is capable of using 2-butene-1,4-diol as a starting raw material, and synthesizing the 3-hydroxymethyltetrahydrofuran through a three-step reaction of dehydration cyclization, hydroformylation and reduction. The production technology is moderate in reaction conditions, low in cost, less in three wastes, and suitable for the industrial production.
Robust cobalt oxide catalysts for controllable hydrogenation of carboxylic acids to alcohols
Song, Song,Wang, Dong,Di, Lu,Wang, Chuanming,Dai, Weili,Wu, Guangjun,Guan, Naijia,Li, Landong
, p. 250 - 257 (2018/02/20)
The selective catalytic hydrogenation of carboxylic acids is an important process for alcohol production, while efficient heterogeneous catalyst systems are still being explored. Here, we report the selective hydrogenation of carboxylic acids using earth-abundant cobalt oxides through a reaction-controlled catalysis process. The further reaction of the alcohols is completely hindered by the presence of carboxylic acids in the reaction system. The partial reduction of cobalt oxides by hydrogen at designated temperatures can dramatically enhance the catalytic activity of pristine samples. A wide range of carboxylic acids with a variety of functional groups can be converted to the corresponding alcohols at a yield level applicable to large-scale production. Cobalt monoxide was established as the preferred active phase for the selective hydrogenation of carboxylic acids.
Preparation method of tetrahydro-3-furanmethanol
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Paragraph 0008, (2018/04/02)
The invention relates to the field of preparation of insecticides, in particular to a preparation method of tetrahydro-3-furanmethanol. The method comprises the steps as follows: 13.6 g of sodium ethoxide and 0.5 g of sodium iodide are dissolved in 120 mL of absolute ethyl alcohol, 32 g of diethyl malonate is dropwise added in an ice-water bath, the temperature is controlled at 20 DEG C or below,stirring is performed continuously for 1 h after addition, then 30.3 g of ethyl bromoacetate is slowly added, the temperature is increased to 50-60 DEG C after addition, stirring is performed for about 8 h, ethyl bromoacetate is detected to be used up through gas chromatography, a heating reaction is stopped, the system is cooled to the room temperature, 10 mL of a saturated ammonium chloride solution is added with stirring, the system is adjusted to be neutral or slightly acid, solvent ethyl alcohol is evaporated, residues are dissolved in 100 mL of water and 100 mL of ethyl acetate for extraction, solution separation is performed, an organic phase is separated, the solvent ethyl acetate is removed from the organic phase, reduced pressure distillation is performed through an oil pump, andthe first fraction point, namely, a triethyl 1,1,2-ethanetricarboxylate product, is collected. The process is simple, safety in actual production is guaranteed, and the product with higher yield is obtained.
Insecticide dinotefuran intermediate 3 - hydroxy methyl tetrahydrofuran synthetic method
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, (2018/04/01)
The invention discloses a synthetic method of pesticide dinotefuran intermediate 3-hydroxymethyl tetrahydrofuran, and the synthetic method is as follows: reacting compound succinic acid dialkyl ester with formic acid alkyl ester in the presence of a strong alkali to obtain a compound III, then obtaining a compound II by a reduction reaction, finally, in the presence of an acid catalyst, obtaining a compound shown as formula I by a dehydration cyclization reaction, and R or R ' respectively independently represents C1-5 alkyl. The synthetic method is low in raw material cost, simple in reaction operation, less in pollution, high in yield of each step, 99% in the yield of the reducing step, and suitable for industrial production.
Selective Hydrogenation of Carboxylic Acids to Alcohols or Alkanes Employing a Heterogeneous Catalyst
Ullrich, Johannes,Breit, Bernhard
, p. 785 - 789 (2018/02/14)
The chemoselective hydrogenation of carboxylic acids to either alcohols or alkanes is reported, employing a heterogeneous bimetallic catalyst consisting of rhenium and palladium supported on graphite. α-Chiral carboxylic acids were hydrogenated without loss of optical purity. The catalyst displays a reverse order of reactivity upon hydrogenation of different carboxylic functions with esters being less reactive than amides and carboxylic acids. This allows for chemoselective hydrogenation of an acid in the presence of an ester or an amide function.
A synthetic method of the dinotefuran (by machine translation)
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Paragraph 0049; 0068; 0087, (2017/08/27)
The invention discloses a method for synthesis of dinotefuran, to γ - butyrolactone as raw materials, by Aldol condensation, also the original two-step by the reaction of 3 - hydroxy methyl tetrahydrofuran, then by the Gabriel synthesis of 3 - tetrahydrofuran methyl amine, dimethyl carbonate (DMC) as methylation reagent with the urea synthesis O - methyl isourea, re-nitration synthetic O - methyl - N - nitro-isourea, then with the methylamine reaction synthesis of 1, 3 - dimethyl - 2 - nitro-isourea, final 3 - tetrahydrofuran methylamine with 1, 3 - dimethyl - 2 - nitro-isourea through SN2 Bimolecular nucleophilic substitution reaction, one-step synthesis of dinotefuran. The present invention uses non of dimethyl carbonate as the methylating reagent, the methylation reaction yield ≥ 95%, O - methyl isourea content ≥ 96%, the by-product is carbon dioxide and methanol, process and environmental protection, the overall yield of the dinotefuran ≥ 50%. Synthetic method of this invention to reduce the production cost at the same time, with three wastes, after treatment is simple, the advantages of the environment friendly, and is suitable for industrial production, bring about significant economic benefits. (by machine translation)
Synthesis method of tetrahydro-3-furfuryl alcohol
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Paragraph 0030, (2017/09/18)
The invention discloses a synthesis method of tetrahydro-3-furfuryl alcohol, and solves the problems of complicated route, operation difficulty, many three wastes and high cost of 3-hydroxymethyl-tetrahydrofuran synthesis in the prior art. The method comprises the following steps of (1) in an organic solvent, performing reaction on malonic acid and chlorohydrin under the existence of a catalyst A to produce ethyl oxalyl chloride; (2) performing closed loop reaction on the ethyl oxalyl chloride under the alkali effect to produce 3-formic acid-gamma-butyrolactone; (3) performing reduction and purification on the 3-formic acid-gamma-butyrolactone under the conditions of a reducing agent and a catalyst B to obtain 3-hydroxymethyl-tetrahydrofuran. The synthesis method has the advantages that the post treatment is simple; green and environment-friendly effects are achieved; the cost is low; the operation is simple; the yield is high, and the like.
