82027-51-8

Upstream product

• 19255-01-7 2-oxo-1,2-diphenylethylmethanesulfonate 
• 141-53-7 sodium formate 
• 64-18-6 formic acid 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 109-94-4 formic acid ethyl ester 
• 134-81-6 benzil 
• 122-52-1 triethyl phosphite 
• 121-45-9 phosphorous acid trimethyl ester 
• 102-85-2 tri-n-butyl phosphite 
• 3491-28-9 2-diethylphosphoryloxy-1,2-diphenylethanone 

Downstream Products

• 4252-31-7 N-formylbenzamide 
• 451-40-1 phenyl benzyl ketone 
• 4675-18-7 4,5-diphenyloxazole 

Relevant academic research and scientific papers

Compact reaction-module on a pad for scalable flow-production of organophosphates as drug scaffolds

Continuous pharmaceutical manufacturing receives intense attention as an alternative way to meet flexible market needs with the assurance of higher safety and quality control. Here, we report a compact reaction-module on a pad (CRP, 170 × 170 × 1.2 mm) for scale-up production of drug precursors in a continuous-flow. The CRP system was devised by stacking 9 films of the patterned polyimide to integrate micro-flow circuits, combining the functions of the even distribution of feeds, being completely mixed in less than a few milliseconds. A methodology of using a highly reactive species for the single-step synthesis of α-phosphonyloxy ketone, a drug scaffold, required the synthesis time of a few seconds in microfluidics. The fast reaction in the single CRP was capable of producing 19.2 g h-1 drug precursor, which indicates a solid step toward kilogram-scale pharmaceutical manufacturing in small footage.

Fast-Synthesis of α-Phosphonyloxy Ketones as Drug Scaffolds in a Capillary Microreactor

A simple, room temperature approach for the fast single-step synthesis of α-phosphonyloxy ketone, a drug scaffold, has been developed which involves highly reactive species i.e., 1,2-dicarbonyls that readily react with trialkyl phosphites and formic acids in batch as well as in continuous-flow with the flow rate of 3 ml/min (tR = ～4 s). The present approach reduced the synthesis time from hours to minutes in batch, which was further lowered to a few seconds precisely controlled by single capillary microfluidics. A wide range of 1,2-dicarbonyl derivatives were smoothly transformed to their corresponding α-phosphonyloxy ketones in moderate to good yields (50–82 %) under optimized flow-reaction conditions. Further, the α-phosphonyloxy ketones produced can be utilized in batch process to form benzoin, oxazole core, and α,α′-diarylated carbonyl compounds in 82 %, 50 %, and 54 % yields, respectively, which are alternative key precursors/scaffolds of natural products and active pharmaceutical ingredients (APIs).

Polyvinylpolypyrrolidoniume tribromide as new and metal-free catalyst for the formylation and trimethylsilylation of hydroxyl group

Trimethylsilylation of alcohols was achieved using 1,1,1,3,3,3- hexamethyldisilazane (HMDS) as silylating agent, in the presence of polyvinylpolypyrrolidoniume tribromide in acetonitrile at room temperature. Also a variety of alcohols were converted into alkyl formates by ethyl formate and a catalytic amount of polyvinylpolypyrrolidoniume tribromide under solvent free conditions at room temperature.

Ceric ammonium nitrate promoted oxidation of oxazoles

The ceric ammonium nitrate promoted oxidations of 4,5-diphenyloxazoles and oxazoles with various substitution patterns have been investigated. This transformation results in the formation of the corresponding imide in good yield and tolerates a wide variety of functional groups and substituents on the oxazole moiety.

Novel catalytic acetylation and formylation of alcohols with potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O)

Acetylation and formylation reactions of alcohols with ethyl acetate, acetic acid and ethyl formate were catalyzed with potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O) in a mild, efficient and convenient method with high to excellent yields.

A convenient and chemoselective acetylation and formylation of alcohols and phenols using acetic acid and ethyl formate in the presence of Bi(III) salts

A variety of alcohols are acetylated and formylated efficiently with acetic acid and ethyl formate in the presence of catalytic amounts of Bi(III) salts such as BiCl3, Bi(TFA)3 and Bi(OTf)3. BiCl3 and Bi(OTf)3 are also effective catalysts for acetylation of phenols. All of these catalysts are ineffective in formylation of phenols. Selective acetylation and formylation of alcohols in the presence of phenols is an additional advantage of this procedure.

Gas-phase pyrolysis in organic synthesis. Part 2. Novel rearrangement of esters and ethers into aryl ketones

The formate ester of benzoin (1) and the methyl ethers of benzoin and anisoin (2, 3) have been converted separately under thermal gas-phase conditions cleanly into 1,2-diarylethanone and have given, respectively, the following Arrhenius log A (s-1) and Ea (kJ mol-1): 10.11 and 132.0, 11.29 and 173.0, and 11.85 and 151.1. A plausible mechanism is suggested to account for these transformations based on the kinetics and products of reaction.

Convenient syntheses of 2-alkyl(Aryl)-4,5-diphenyloxazoles and 2-alkyl(Aryl)-4-phepyloxazoles

The synthetic methods to prepare 2-alkyl(aryl)-4,5-diphenyloxazoles and 2-alkyl(aryl)-4-phenyloxazoles were improved on the basis of a mechanistic study of oxazole formation from α-hydroxy ketones (carboxylic esters of benzoin and phenacyl alcohols). By these methods, seven trisubstituted oxazoles and twelve disubstituted oxazoles of the title compounds were prepared.