265661-38-9

Upstream product

• 2085-88-3 2-methyl-2-phenyloxirane 
• 96-22-0 pentan-3-one 
• 208466-71-1 2-chloromethyl-3-(2-methoxyethoxy)prop-1-ene 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Straight and versatile synthesis of substituted perhydrofuro[2,3-b]pyrans from 2-chloromethyl-3-(2-methoxyethoxy)propene

The reaction of 2-chloromethyl-3-(2-methoxyethoxy)propene with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E1=R1R2CO) in THF at -78 to 0°C, followed by the addition of an epoxide [E2=R3R4C(O)CHR5] at 0 to 20°C leads, after hydrolysis, to the expected methylidenic diols. These diols when subjected to successive hydroboration-oxidation and further oxidation, spontaneous cyclization occurs to furnish a series of differently substituted perhydrofuro[2,3-b]pyrans.

Substituted perhydrofuropyrans: Easy preparation from 2-chloromethyl-3- (2-methoxyethoxy)propene through 3-methylene-1,6-diols

The reaction of 2-chloromethyl-3-(2-methoxyethoxy)prop-1-ene (1) with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E1=R1R2CO) in THF at -78 to 0°C, followed by treatment with an epoxide [E2=R3R4C(O)CHR5] at 0 to 20°C leads, after hydrolysis, to the expected unsaturated diols 2. When some compounds 2 (2e-h) are successively hydroborated (BH3 · THF) and oxidised (33% H2O2 and then PCC), the expected perhydrofuropyrans 3e-h are isolated directly. (C) 2000 Elsevier Science Ltd.