Ethyl /3-ethoxyethyl carbonate

Ethoxybenzene 2-Ethoxyethanol 2-Ethoxyethyl acetate Ethyl acetate Ethyl acrylate Ethylamine gauche) Ethylamine trans) Ethylamine average) Ethylbenzene Ethyl benzoate Ethyl butanoate Ethyl ra 5-cinnamate Ethyl cyanate Ethyl cyanoacetate Ethylene carbonate Ethylene glycol average) Ethyleneimine Ethylene-sulfur dioxide complex... 

Acetone, acetic acid (glacial), lower alcohols, alcohol/ diethyl ether, amyl acetate, M-butyl acetate, butyl lactate, 7-butyrolactin, cyclopentanone, diethyl acetate, diethyl ketone, N,N-dimethylacetamide, dimethyl carbonate, dimethyl cyanamide, dimethylformamide, dimethyl maleate, dimethylsulfoxide, 2-ethoxyethyl acetate, ethyl acetate, ethyl amyl ketone, ethylene glycol ethers, ethyl lactate, 2-hexanone, methyl acetate, methyl ethyl ketone, methyl propyl ketone, M-methylpyrrolidone-2, 2-octanone, 1-pentanone, M-pentyl acetate, pyridine ... 

The group at Merck, Inc. formylated ethyl 3-ethoxypropanoate at the a-carbon with ethyl formate in the presence of ethoxide and then treated the resulting aldehydic ester with the amidine from acetamide. The resulting 4-hydroxy-5-( 3-ethoxyethyl)-2-methylpyrimidine yielded the corresponding 4-chloroderivative with phosphorus oxychloride, which, with ethanohc ammonia produced the 4-amino-5-(P-ethoxyethyl)-2-methylpyrimidine. Ether cleavage to the P-bromohydrobromide produced the immediate precursor to the thiamine hydrobromide (Scheme 12.91). 

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