Encyclopedia of Reagents for Organic Synthesis 2001
DOI: 10.1002/047084289x.rf028
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N-Formylimidazole

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“…The resulting oligodeoxynucleotide solution was reduced to a volume of 500 μL using a Speed-Vac concentrator (Genevac Ltd, UK). Then 25 μL of 2-mercaptoethanol and 25 μL of triethylamine were added to the mixture, followed by 1 mL of freshly prepared formylimidazole 30,49 (1 M in THF), which was added in portions over the course of 2 h. When the aminopyrimidine oligodeoxynucleotides had completely disappeared, as confirmed by MS analysis, the reaction mixture was evaporated to remove organic solvents and purified on a Sep-Pak C18 Classic cartridge with 360 mg sorbent.…”
Section: Methodsmentioning
confidence: 99%
“…The resulting oligodeoxynucleotide solution was reduced to a volume of 500 μL using a Speed-Vac concentrator (Genevac Ltd, UK). Then 25 μL of 2-mercaptoethanol and 25 μL of triethylamine were added to the mixture, followed by 1 mL of freshly prepared formylimidazole 30,49 (1 M in THF), which was added in portions over the course of 2 h. When the aminopyrimidine oligodeoxynucleotides had completely disappeared, as confirmed by MS analysis, the reaction mixture was evaporated to remove organic solvents and purified on a Sep-Pak C18 Classic cartridge with 360 mg sorbent.…”
Section: Methodsmentioning
confidence: 99%
“…To gain some insight into the reaction mechanism of this formylation process, control experiments were conducted with 4-iodoanisole as the substrate (Scheme 3 ). Treatment of 1 with freshly prepared 1 H -imidazole-1-carbaldehyde ( A ; contaminated with some imidazole), 17 in the presence of Pd 2 dba 3 and Et 3 N in DMF at 70 °C gave aldehyde 2 in 85% isolated yield. Additionally, heating of A in the presence of Et 3 N in DMF resulted in the generation of carbon monoxide, as confirmed by a chemical method 18 (see Supporting Information): this indicated that A , which is formed by the reaction of CDI with formic acid, acts as the source of carbon monoxide.…”
Section: Table 1 Optimization Of the Reaction Condition...mentioning
confidence: 99%