Journal of Organic Chemistry p. 731 - 735 (1991)
Update date:2022-08-03
Topics:
Katoh, Akira
Lu, Tianbao
Devadas, B.
Adams, Steven P.
Gordon, Jeffrey I.
Gokel, George W.
The reaction of 5-ethoxypentan-1-ol with a variety of 5-halovalerate alkyl esters afforded ester exchange products rather than the expected products of Williamson ether synthesis.The virtually unknown reaction of an alkoxide with a 5-halovalerate ester contrasts strongly with literature reports of reactions involving other nucleophiles in which the halogen substitution products are nearly always isolated.An explanation is offered for this behavior in terms of a chelation-induced conformation of the substrate.Although the direct synthetic approach failed, the hitherto unknown title compound could still be prepared, albeit in six steps in 6percent overall yield.The approach used is discussed along with the interesting chemistry of this system.
View MoreSuzhou CarbonWell Pharma-Tech Co., Ltd
Contact:Tel: + 86 (0)512-8898-1216; + 86-18606258602
Address:2358 Changan Road, Wujiang Scientific Innovation Park, Wujiang, Jiangsu Province, P. R. China 215200
Taizhou Shengxing Chempharm Co.,Ltd
Contact:+86-576-88516600
Address:Yantou Chemical Zone Jiaojiang Taizhou Zhejiang China
Hubei Lingsheng Pharmaceuticals Co., Ltd.
Contact:+86-0710-3538058
Address:Xiangyang City Xiangcheng Economic Development Zone, Hubei Province
Golden Union Agrochemical Import and Export Co., Ltd.
Contact:86-755-23910527
Address:Room 1106, Tower 3A, Excellence Century Center, Futian District, Shenzhen, China
SHENZHEN PENGCHENG REDSTAR INDUSTRY CO.,LTD
Contact:+86-755-82412922
Address:Room 8066, East Block, Square City, Jiabin Road, Luohu District
Doi:10.1248/cpb.22.2987
(1974)Doi:10.1016/S0040-4039(01)91885-4
(1974)Doi:10.1007/BF00921285
()Doi:10.1016/S0022-328X(00)98136-1
(1976)Doi:10.1055/s-1974-23465
(1974)Doi:10.1016/S0960-894X(02)01048-X
(2003)