85891-86-7

Upstream product

• 85891-82-3 2-(phenylmethoxy)-α-methylstyrene 
• 85891-85-6 ethyl 3-<4-<2-(phenylmethoxy)phenyl>pyridin-3-yl>propenoate 
• 85891-84-5 4-<2-(phenylmethoxy)phenyl>pyridine-3-carboxaldehyde 
• 87307-75-3 2-(2-Benzyloxy-phenyl)-propan-2-ol 
• 118-93-4 o-hydroxyacetophenone 
• 31165-67-0 2'-benzyloxyacetophenone 
• 85891-85-6 (E)-3-[4-(2-Benzyloxy-phenyl)-pyridin-3-yl]-acrylic acid ethyl ester 
• 87307-76-4 ethyl 3-<4-<2-(phenylmethoxy)phenyl>pyridin-3-yl>propanoate 

Downstream Products

• 85891-87-8 4-<2-(2-ethoxy-2-oxoethoxy)phenyl>-1-methyl-3-(3-oxo-3-ethoxypropyl)pyridinium iodide 
• 87307-94-6 4-(2-hydroxyphenyl)-1-methyl-3-(3-oxo-3-ethoxypropyl)pyridinium iodide 

Relevant academic research and scientific papers

Synthesis of 3-Methyl-5,6-dihydro-3H-benzofuroisoquinolin-7(7aH)-ones

The coupling of 2-(alkoxymethoxy)phenylcopper derivatives with the salt of ethyl chloroformate and ethyl 3-(pyridin-3-yl)propenoate was found to be an efficient method for the preparation of 4-(2-hydroxyphenyl)pyridines 13 substituted at C-3 with a propanoate side chain.N-Methylation and O-alkylation with ethyl bromoacetate gave salts 3 which when treated with base underwent an intramolecular enolate addition to the pyridinium nucleus to produce spiro 4.Prolonged base treatment of 4 yielded ethyl 3-methyl-7-hydroxy-5,7a-dihydro-3H-benzofuroisoquinoline-6-carboxylates 5 by a Dieckmann reaction.Reduction of 5 led to predominately trans-3-methylhexahydro-1H-benzofuroisoquinolin-7(7aH)-ones, while reduction of 4 and then Dieckmann cyclization yielded mainly the cis isomers.

SYNTHESIS OF 3-METHYL-2,3,4,4a,5,6-HEXAHYDRO-1H-BENZOFUROISOQUINOLINE-7(7aH)-ONES

The 2,3,4,4a,5,6-hexahydro-1H-benzofuroisoquinoline-7(7aH)-one ring system is prepared from a 4-arylpyridine precursor by sequential intramolecular enolate addition to a pyridinium ion, Dieckmann cyclization, and catalytic hydrogenation.