The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Peroxide-induced reduction of 9,10-anthraquinone by sodium borohydride in diglyme》. Authors are Panson, Gilbert S.; Weill, C. Edwin.The article about the compound:(2-Methylthiazol-4-yl)methanolcas:76632-23-0,SMILESS:OCC1=CSC(C)=N1).Related Products of 76632-23-0. Through the article, more information about this compound (cas:76632-23-0) is conveyed.
9,10-Anthraquinone (I) is not reduced at 20° by NaBH4 in pure diglyme [O(CH2CH2OMe)2] (II). In the presence of peroxides I is reduced to 9,10-anthradiol (III). When 0.25 g. NaBH4 is added to 1 g. I in 20 cc. II which has been exposed to air for several weeks a vigorous exothermic reaction sets in and the solution turns deep red. The mixture is stirred in an Ar atm. 45 min. and poured into 500 cc. cold N HCl, causing the precipitation of 0.9 g. III, m. 157-80°, which, on recrystallization from EtOH, yields I again. In a similar experiment, treating the reaction mixture with 5 cc. Ac2O and 3 g. fused NaOAc, heating it 0.5 hr. at 70° in an Ar atm., and pouring it into ice-H2O give 0.8 g. III diacetate, needles, m. 268-71° (decomposition). A possible mechanism for the peroxide-promoted reduction may be the cleavage of the solvent to aldehydes by a peroxide-induced action followed by conversion of the aldehydes so formed to alkoxyborohydrides which are the effective reducing agents.
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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem