Реакция #1679035

Уравнение реакции

tributylphosphine

4,4-dithiodibutyric acid

dioxane

triphenylmethanol

→

4-tritylthio-butyric acid

Выход 50.0%

Растворители

water

DMF

Условия реакции

Обработка

1. 1
   ДругоеAfter removing the solvents in vacuo the crude product
2. 2
   workup.STIRRINGthe solution was stirred for 30 minutes at 60° C
3. 3
   ТемператураAfter the solution was cooled to ambient temperature
4. 4
   workup.ADDITION580 μl (4.6 mmol) borontrifluor etherate was added
5. 5
   workup.STIRRINGthe reaction mixture was stirred overnight at 80° C
6. 6
   КонцентрированиеThe solution was concentrated in vacuo
7. 7
   Другоеthe product purified by column chromatography (silica, eluent: ethyl acetate/hexane 1:1 v/v)
8. 8
   ДругоеAfter recrystalization from ethyl acetate/hexane the product
9. 9
   Другоеwas obtained as white needles with a yield of 50%

Методика

A solution of 0.48 g (2 mmol) 4,4-dithiodibutyric acid in freshly distilled dioxane (20 ml) was stirred under a nitrogen atmosphere. Then 0.52 ml (2.1 mmol) tributylphosphine and 50 μl water were added and the reaction mixture was stirred for 4 hours at room temperature. After removing the solvents in vacuo the crude product was dissolved in 25 ml DMF together with 1.15 g (4.4 mmol) triphenylmethanol, and the solution was stirred for 30 minutes at 60° C. After the solution was cooled to ambient temperature, 580 μl (4.6 mmol) borontrifluor etherate was added and the reaction mixture was stirred overnight at 80° C. The solution was concentrated in vacuo and the product purified by column chromatography (silica, eluent: ethyl acetate/hexane 1:1 v/v). After recrystalization from ethyl acetate/hexane the product was obtained as white needles with a yield of 50%.

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