Premium
Synthese von 15‐Hydroxy[9]metacyclophan
Author(s) -
LorenziRiatsch Annalaura,
Wälchli Rudolf,
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.19850680813
Subject(s) - chemistry , yield (engineering) , aldehyde , aldol reaction , amine gas treating , nitro , medicinal chemistry , stereochemistry , organic chemistry , catalysis , materials science , alkyl , metallurgy
Synthesis of 15‐Hydroxy[9]metacyclophane 3‐(1‐Nitro‐2‐oxocyclododecyl)propanal ( 1 ) was converted to 15‐hydroxy[9]metacyclophane ( 3 ) on two different routes. In the first case the internal aldol reaction product of 1 was treated with K 2 CO 3 /THF to give 3 in 29 % yield with regard to cyclododecanone. Alternatively, the aldehyde 1 reacted with a primary amine to form e.g. 4 which gave 3 in the presence of CH 3 I/K 2 CO 3 in 48 % yield.