85733-07-9

Upstream product

• 37170-49-3 trimethylsilyl 2,2-dimethylpropionate 
• 141809-67-8 1-methyl-3-phenylpropyl trimethylsilyl ether 
• 150272-59-6 1-methyl-3-phenylpropyl tert-butyldimethylsilyl ether 
• 2344-70-9 1-phenyl-3-butanol 
• 3282-30-2 pivaloyl chloride 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 75-98-9 Trimethylacetic acid 
• 434935-69-0 2-methyl-6-nitrobenzoic anhydride 

Downstream Products

• 2344-70-9 1-phenyl-3-butanol 

Relevant academic research and scientific papers

Deoxyfluorination with CuF2: Enabled by Using a Lewis Base Activating Group

Deoxyfluorination is a primary method for the formation of C?F bonds. Bespoke reagents are commonly used because of issues associated with the low reactivity of metal fluorides. Reported here is the development of a simple strategy for deoxyfluorination, using first-row transition-metal fluorides, and it overcomes these limitations. Using CuF2 as an exemplar, activation of an O-alkylisourea adduct, formed in situ, allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF2. The utility of the process in enabling 18F-radiolabeling is also presented.

A new method for the synthesis of carboxylic esters and lactones with di-2-thienyl carbonate (2-DTC) by the promotion of DMAP and iodine

The esterification of carboxylic acids with alcohols by using di-2-thienyl carbonate (2-DTC) in the presence of a catalytic amount of 4-(dimethylamino) pyridine (DMAP) proceeded smoothly to afford the corresponding esters in good-to-high yields along with 2(5H)-thiophenone. This esterification was accelerated by the addition of an equimolar amount of iodine to afford the esters in higher yields within a shorter reaction time. Further, cyclization of ω-hydroxycarboxylic acids with an equimolar amount of 2-DTC in the presence of a catalytic amount of DMAP, followed by the addition of 1-4 equimolar amounts of iodine, afforded the corresponding lactones in good-to-high yields under mild conditions. This method was successfully employed in the synthesis of erythro-aleuritic acid lactone.

Efficient method for the esterification of carboxylic acids with alcohols using di-2-thienyl carbonate promoted by catalytic amounts of DMAP and Hf(OTf)4

Esterification of carboxylic acids with alcohols including bulky secondary ones by using an equimolar amount of di-2-thienyl carbonate (2-DTC) in the presence of a catalytic amount of 4-(dimethylamino)pyridine (DMAP) followed by addition of a catalytic amount of hafnium(IV) trifluoromethanesulfonate (Hf(OTf)4) afforded the corresponding esters in good to high yields. Copyright

An effective method for the synthesis of carboxylic esters and lactones using substituted benzoic anhydrides with Lewis acid catalysts

An efficient mixed-anhydride method for the synthesis of carboxylic esters and lactones using benzoic anhydride having electron withdrawing substituent(s) is developed by the promotion of Lewis acid catalysts. In the presence of a catalytic amount of TiCl2(ClO4)2, various carboxylic esters are prepared in high yields through the formation of the corresponding mixed-anhydrides from 3,5-bis(trifluoromethyl)benzoic anhydride and carboxylic acids. The combined catalyst consisting of TiCl 2(ClO4)2 together with chlorotrimethylsilane functions as an effective catalyst for the synthesis of carboxylic esters from free carboxylic acids and alcohols with 4-(trifluoromethyl)benzoic anhydride. Various macrolactones are prepared from the free ω-hydroxycarboxylic acids by the combined use of 4-(trifluoromethyl)benzoic anhydride and titanium(IV) catalysts together with chlorotrimethylsilane under mild reaction conditions. The lactonization of trimethylsilyl ω-(trimethylsiloxy) carboxylates using 4-(trifluoromethyl)benzoic anhydride is also promoted at room temperature in the presence of a catalytic amount of TiCl 2(ClO4)2. An 8-membered ring lactone, a synthetic intermediate of cephalosporolide D, is successfully synthesized according to this mixed-anhydride method using 4-(trifluoromethyl)benzoic anhydride by the promotion of a catalytic amount of Hf(OTf)4.

Efficient method for the esterification of carboxylic acids with alcohols using di-2-thienyl carbonate promoted by DMAP and iodine

Reaction of carboxylic acids with alcohols by using an equimolar amount of di-2-thienyl carbonate (2-DTC) in the presence of a catalytic amount of 4-(dimethylamino)pyridine (DMAP) followed by addition of an equimolar amount of iodine proceeded smoothly to afford the corresponding esters and 2(5H)-thiophenone in good to high yields.

An Effective Use of Benzoic Anhydride and Its Derivatives for the Synthesis of Carboxylic Esters and Lactones: A Powerful and Convenient Mixed Anhydride Method Promoted by Basic Catalysts

Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2-methyl-6-nitrobenzoic anhydride with triethylamine by the promotion of a basic catalyst such as 4-(dimethylamino)pyridine. A variety of lactones are also prepared in high yields at room temperature from the corresponding ω-hydroxycarboxylic acids with use of 2-methyl-6-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine. A similar reaction occurs with triethylamine when using a catalytic amount of 4-(dimethylamino)pyridine 1-oxide as an effective promoter for the intramolecular condensation reaction. These methods are successfully applied to the synthesis of erythro-aleuritic acid lactone and an eight-membered-ring lactone moiety of octalactins A and B. The efficiency of the cyclizations is compared to those of other reported lactonizations.

A Useful Method for the Preparation of Carboxylic Esters from Free Carboxylic Acids and Alcohols

Various carboxylic esters are prepared in excellent yields from nearly equimolar amounts of free carboxylic acids and alcohols at room temperature by combined use of 4-(trifluoromethyl)benzoic anhydride and a catalytic amount of active titanium(IV) salt together with chlorotrimethylsilane.

A New and Efficient Esterification Reaction via Mixed Anhydrides by the Promotion of a Catalytic Amount of Lewis Acid

In the presence of a catalytic amount of Lewis acid, various carboxylic esters or S-phenyl carbothioates are prepared in excellent yields by the respective reactions of equimolar amounts of silyl carboxylates and alkyl silyl ethers or phenyl silyl sulfides with 4-trifluoromethylbenzoic anhydride.

An Efficient Method for the Preparation of Carboxylic Esters via Mixed Anhydrides by the Promotion of a Catalytic Amount of Lewis Acid

Various carboxylic esters are prepared in excellent yields by the reaction of nearly equimolar amounts of silyl derivatives of carboxylic acids and alcohols with p-trifluoromethylbenzoic anhydride in the presence of a catalytic amount of Lewis acid.

FACILE METHOD FOR THE ACYLATION OF ALCOHOLS AND AMIDES BY THE USE OF 1,1'-DIMETHYLSTANNOCENE AND ACYL CHLORIDES

Acylation of alcohols and amides was effected under mild conditions by the use of 1,1'-dimethylstannocene and acyl chlorides, giving the corresponding esters and imides in good to excellent yields.