Реакция #57985

Уравнение реакции

Diisopropyl azodicarboxylate

5-hydroxybenzofuran-2-carboxylic acid methyl ester

triphenylphosphine

1-(2-hydroxyethyl)-pyrrolidine

→

5-(2-pyrrolidin-1-yl-ethoxy)benzofuran-2-carboxylic acid methyl ester

Выход 58.2%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеthe solvent was removed
2. 2
   workup.DISSOLUTIONthe residue was dissolved in a 2:1 mixture of Et2O
3. 3
   ПромывкаThe solution was washed with 1.0M aqueous NaOH
4. 4
   ЭкстракцияThe product was extracted into 1.0 M hydrochloric acid
5. 5
   Промывкаthe combined acid extracts were washed with Et2O
6. 6
   ТемператураThe extracts were cooled
7. 7
   ЭкстракцияThe basic solution was extracted with CH2Cl2
8. 8
   Сушкаthe organic layer was dried over anhydrous MgSO4
9. 9
   Концентрированиеconcentrated

Методика

Anhydrous tetrahydrofuran (15 ml) was added to a mixture of 5-hydroxybenzofuran-2-carboxylic acid methyl ester (1.10 g, 5.7 mmol), triphenylphosphine (1.50 g, 5.7 mmol), and 1-(2-hydroxyethyl)-pyrrolidine (0.66 g, 5.7 mmol) under a nitrogen atmosphere. Diisopropyl azodicarboxylate (1.15 ml, 5.8 mmol) was slowly added to the solution at room temperature. After 2 days, the solvent was removed and the residue was dissolved in a 2:1 mixture of Et2O:EtOAc (150 ml). The solution was washed with 1.0M aqueous NaOH. The product was extracted into 1.0 M hydrochloric acid and the combined acid extracts were washed with Et2O. The extracts were cooled and the pH of the extracts was adjusted to pH 12 with 50% aqueous NaOH. The basic solution was extracted with CH2Cl2 and the organic layer was dried over anhydrous MgSO4, and concentrated to give 5-(2-pyrrolidin-1-yl-ethoxy)benzofuran-2-carboxylic acid methyl ester (0.96 g) as an amber colored solid.

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