(2,6-Dichloro-4-alkoxyphenyl)-(2,4-dichlorophenyl)methyl trichloroacetimidates

Protection of alcohols and carboxylic acids in solution or on polymer support

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

(2,6-Dichloro-4-methoxyphenyl)-(2,4-dichlorophenyl)-methyl trichloroacetimidate can be efficiently activated by TMSOTf (10-100 mol%) to react with alcohols and carboxylic acids. Under these conditions a wide variety of alcohols can be transformed into the corresponding ethers in excellent yields with a slight excess of the trichloroacetimidate. The resulting ethers are not susceptible to typical deprotection conditions for benzyl and 4-methoxybenzyl ether groups, however, they can be conveniently deprotected by treatment with 30-50% trifluoroacetic acid in dichloromethane. Polymer-bound (2,6-dichloro-4-alkoxyphenyl)-(2,4-dichlorophenyl)methyl trichloroacetimidate is useful for immobilization of alcohols and carboxylic acids.

Original languageEnglish (US)
Pages (from-to)3633-3641
Number of pages9
JournalSynthesis
Issue number21
DOIs
StatePublished - 2009
Externally publishedYes

Fingerprint

Carboxylic Acids
Carboxylic acids
Ethers
Polymers
Alcohols
Trifluoroacetic acid
Trifluoroacetic Acid
Methylene Chloride
Dichloromethane
Ether
trichloroacetamide

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Catalysis

Cite this

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title = "(2,6-Dichloro-4-alkoxyphenyl)-(2,4-dichlorophenyl)methyl trichloroacetimidates: Protection of alcohols and carboxylic acids in solution or on polymer support",
abstract = "(2,6-Dichloro-4-methoxyphenyl)-(2,4-dichlorophenyl)-methyl trichloroacetimidate can be efficiently activated by TMSOTf (10-100 mol{\%}) to react with alcohols and carboxylic acids. Under these conditions a wide variety of alcohols can be transformed into the corresponding ethers in excellent yields with a slight excess of the trichloroacetimidate. The resulting ethers are not susceptible to typical deprotection conditions for benzyl and 4-methoxybenzyl ether groups, however, they can be conveniently deprotected by treatment with 30-50{\%} trifluoroacetic acid in dichloromethane. Polymer-bound (2,6-dichloro-4-alkoxyphenyl)-(2,4-dichlorophenyl)methyl trichloroacetimidate is useful for immobilization of alcohols and carboxylic acids.",
author = "Michio Kurosu and Kai Li",
year = "2009",
doi = "10.1055/s-0029-1216974",
language = "English (US)",
pages = "3633--3641",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "21",

}

TY - JOUR

T1 - (2,6-Dichloro-4-alkoxyphenyl)-(2,4-dichlorophenyl)methyl trichloroacetimidates

T2 - Protection of alcohols and carboxylic acids in solution or on polymer support

AU - Kurosu, Michio

AU - Li, Kai

PY - 2009

Y1 - 2009

N2 - (2,6-Dichloro-4-methoxyphenyl)-(2,4-dichlorophenyl)-methyl trichloroacetimidate can be efficiently activated by TMSOTf (10-100 mol%) to react with alcohols and carboxylic acids. Under these conditions a wide variety of alcohols can be transformed into the corresponding ethers in excellent yields with a slight excess of the trichloroacetimidate. The resulting ethers are not susceptible to typical deprotection conditions for benzyl and 4-methoxybenzyl ether groups, however, they can be conveniently deprotected by treatment with 30-50% trifluoroacetic acid in dichloromethane. Polymer-bound (2,6-dichloro-4-alkoxyphenyl)-(2,4-dichlorophenyl)methyl trichloroacetimidate is useful for immobilization of alcohols and carboxylic acids.

AB - (2,6-Dichloro-4-methoxyphenyl)-(2,4-dichlorophenyl)-methyl trichloroacetimidate can be efficiently activated by TMSOTf (10-100 mol%) to react with alcohols and carboxylic acids. Under these conditions a wide variety of alcohols can be transformed into the corresponding ethers in excellent yields with a slight excess of the trichloroacetimidate. The resulting ethers are not susceptible to typical deprotection conditions for benzyl and 4-methoxybenzyl ether groups, however, they can be conveniently deprotected by treatment with 30-50% trifluoroacetic acid in dichloromethane. Polymer-bound (2,6-dichloro-4-alkoxyphenyl)-(2,4-dichlorophenyl)methyl trichloroacetimidate is useful for immobilization of alcohols and carboxylic acids.

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U2 - 10.1055/s-0029-1216974

DO - 10.1055/s-0029-1216974

M3 - Article

SP - 3633

EP - 3641

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 21

ER -