[基础有机] 经典的有机合成反应------Acid hydrolysis of an acetonide

143 主题	23 好友	5 积分

渐入佳境

Rank: 3 Rank: 3

科研币: 26
速递币: 1578
娱乐币: 8
文献值: 11
资源值: 1
贡献值: 0

发消息

电梯直达

楼主

发表于 2012-10-20 12:20:04 |只看该作者 |倒序浏览

Acid hydrolysis of an acetonide; diols
SyntheticPage 125 (2001)
Submitted 23rd Aug 2001, published 23rd Aug 2001
zac etheridge (zac.etheridge@orange.net),
A contribution from the Caddick Group, Sussex
________________________________________

________________________________________
Chemicals Used
15% HCl (2S)-4-Iodo-3-butyne-1,2-diol Methanol
Procedure
The acetonide (12.51g, 49.6mmol) is stirred in methanol (43mL) at room temperature and the HCl (4.3mL) is added. The reaction is stirred until completion (TLC, 7-8 hours) then carefully quenched with sodium bicarbonate solution, extracted 6 times with ether, washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuum to give an off white solid. Purification can be by column chromatography eluting with 35-100% EtOAc/PE or more conveniently by recrystallisation using 1:1 EtOAc/PE to yield about 10g (90-95%) of white solid.
Author's Comments
This is a very simple and effective method for removal of acetonide groups. Recrystallising the product is easier than column chromatography as the compound takes some time to come off the columnn due to its polarity, and there is invariably a small amount of higher running impurity or starting material at the end.
Data
1H NMR (300MHz, CH3OD) 4.52 (1H, m), 3.66 (2H, m). M.P. 96C
________________________________________
Lead Reference
Hirama M., Iguchi S., Xing G. J. Org. Chem. 2001, 66, 2146.

已有 1 人评分	速递币	收起理由
wangjian2013	+ 10	很给力!

总评分: 速递币 + 10 查看全部评分

淘帖0 收藏0 顶0 踩0

返回列表

[基础有机] 经典的有机合成反应------Acid hydrolysis of an acetonide

分享到：