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Synthese von 12‐Cyano‐15‐hexadecanolid durch Ringerweiterung von 1‐(3′‐Hydroxybutyl)‐2‐oxocyclododecan‐1‐carbonitril
Author(s) -
Milenkov Branimir,
Süsse Manfred,
Hesse Manfred
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680804
Subject(s) - chemistry , yield (engineering) , ring (chemistry) , nitrile , aldehyde , medicinal chemistry , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
Synthesis of 12‐Cyano‐15‐hexadecanolide by Ring Enlargement of 1‐(3′‐Hydroxybutyl)‐2‐oxocyclododecane‐1‐carbonitrile In the presence of Bu 4 NF, 2‐oxocyclododecane‐1‐carbonitrile ( 1 ) reacted with acrylaldehyde to form the corresponding aldehyde 2 which was methylated, e.g. with CH 3 Ti[OCH(CH 3 ) 2 ] 3 . The resulting 1‐(3′‐hydroxybutyl)‐2‐oxocyclododecane‐1‐carbonitrile ( 5 ) was converted to 12‐cyano‐15‐hexadecanolide ( 6 ) in nearly quantitative yield under the influence of Bu 4 NF.