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Silyl Enol Ethers as Protective Groups for Alkyl 4-Halo-3-oxobutanoates in the Arbuzov Reaction with Triethyl Phosphite

Citation

Grosse, AC and Moorhoff, CM, Silyl Enol Ethers as Protective Groups for Alkyl 4-Halo-3-oxobutanoates in the Arbuzov Reaction with Triethyl Phosphite, Heteroatom Chemistry, 8, (4) pp. 361-369. ISSN 1042-7163 (1997) [Refereed Article]

DOI: doi:10.1002/(SICI)1098-1071(1997)8:4<361::AID-HC12>3.0.CO;2-P

Abstract

Alkyl 4-bromo- and 4-chloro-3-oxobutanoates were protected as silyl enol ethers. The Arbnzov reaction of these new compounds with triethyl phosphite gave the corresponding silyl enol phosphonates in high yield. Facile deprotection of the silyl group with water gave alkyl 4-(diethoxyphosphinyl)-3-oxobutanoates in high yields. Protection of 1-methylethyl 4-bromo-3-oxobutanoate as the enol acetate followed by the subsequent reaction with triethyl phosphite gave the corresponding phosphonate in high yield. Deprotection with potassium 2-propoxide gave 1-methylethyl 4-(diethoxyphosphinyl)-3-oxobutanoate in good yield. ©1997 John Wiley & Sons, Inc.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Grosse, AC (Mr Andrew Grosse)
Author:Moorhoff, CM (Dr Moorhoff)
ID Code:12018
Year Published:1997
Web of Science® Times Cited:2
Deposited By:Chemistry
Deposited On:1997-08-01
Last Modified:2011-08-15
Downloads:0

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