Molecules p. 15797 - 15806 (2015)
Update date:2022-08-16
Topics:
Manansala, Camille
Tranmer, Geoffrey K.
A series of simple 2-methylpyridines were synthesized in an expedited and convenient manner using a simplified bench-top continuous flow setup. The reactions proceeded with a high degree of selectivity, producing α-methylated pyridines in a much greener fashion than is possible using conventional batch reaction protocols. Eight 2-methylated pyridines were produced by progressing starting material through a column packed with Raney nickel using a low boiling point alcohol (1-propanol) at high temperature. Simple collection and removal of the solvent gave products in very good yields that were suitable for further use without additional work-up or purification. Overall, this continuous flow method represents a synthetically useful protocol that is superior to batch processes in terms of shorter reaction times, increased safety, avoidance of work-up procedures, and reduced waste. A brief discussion of the possible mechanism(s) of the reaction is also presented which involves heterogeneous catalysis and/or a Ladenberg rearrangement, with the proposed methyl source as C1 of the primary alcohol.
View MoreContact:+8618766299236
Address:ROOM808, BUILDING2,NO.230 SHEN ZHEN ROAD, LAOSHAN DISTRICT
Contact:0572-2722882
Address:1201,F3,xinghuibandao,
Contact:+86-10-62651721
Address:29 Yongxing Road, Daxing District,Beijing China
SHOUGUANG BOYU CHEMICAL CO.,LTD
Contact:+86-536-8256719
Address:ROOM 1101&1103,BUILDING D,ZHONGTU MANSION,NO.6565 EAST FUSHOU STREET,WEIFANG CITY,SHANDONG,CHINA.
Ningbo Inno Pharmchem Co., Ltd.
Contact:86-574-87319282
Address:6F-5,NO.163 RUIQING RD.,NINGBO 315000 CHINA
Doi:10.1021/jo026718+
(2003)Doi:10.1021/acs.oprd.5b00294
(2015)Doi:10.1515/chempap-2015-0036
(2015)Doi:10.1021/acs.inorgchem.6b02270
(2017)Doi:10.1021/ol502207z
(2014)Doi:10.1002/asia.201801529
(2019)