4,4'-Dichlorodibutyl Ether and its Derivatives from Tetrahydrofuran

Acylative Dimerization of Tetrahydrofuran Catalyzed by Rare‐Earth Triflates

“…[23] When aliquots are removed during the addition of THF to acetic anhydride using Yb(OTf) 3 (4 mol%), the ratio of 1a : 2a : higher oligomers does not change substantially. These control experiments rule out an equilibrium process favoring 1a, as has been proposed for the related reaction of THF with phosphorous oxychloride, [7] although there is significant equilibration of the products in the presence of the rare-earth catalysts at the temperatures necessary for distillation. The control experiments employing a rare-earth catalyst were in stark contrast to the results we obtained employing triflic acid (4 mol%) as the catalyst: the ratio of 1a : 2a : higher oligomers changed significantly during the course of the reaction, with greater than 60% yield of higher oligomers at 50% conversion of THF (15 min) to a final product ratio of 25 : 60 : 15 (2 hr).…”

“…For example, the cleavage of tetrahydrofuran with phosphorus oxychloride catalyzed by sulfuric acid gave the dimeric product 1-chloro-4-(4-chlorobutoxy)butane in 70% yield. [7] Acetic anhydride cleavage of tetrahydrofuran catalyzed by HClO 4 , [8] heteropolytungstic acids, [9] or montmorillonite-type earth [10] gave good yields of the dimeric product 4-(4-acetoxybutoxy)butyl acetate (1a) using excess acetic anhydride. Stoichiometric TiCl 4 and excess THF gave 1-chloro-4-(4-chlorobutoxy)butane in 55% yield.…”

Electrospray ionization mass spectrometry study on dipeptide 4‐chlorobutyl ester produced from refluxing of amino acid with phosphoryl chloride in tetrahydrofuran

“…In this paper, positive‐ion‐mode ESI‐MS was applied to trace the process of the reaction of amino acids with phosphoryl chloride in refluxing THF 14, 15. In order to reveal the reaction process, at various time intervals, 0.5 ml of the solution was quenched with water and analyzed by (+)‐ESIMS instantly.…”

A structurally diversified linker enhances the immune response to a small carbohydrate hapten

“…To a solution of 4-(4-hydroxybutoxy)-butanol [37] (110 mg, 0.681 mmol) in CH 2 Cl 2 (10 mL) tert-butyldiphenylsilyl chloride (56.0 mg, 0.203 mmol) was added dropwise under argon at 0°C. After 15 min Et 3 N (8.2 mg, 0.816 mmol) was added and the reaction mixture was allowed to warm up to room temperature and stir overnight.…”