Reaktion #65309

Reaktionsgleichung

DMTr-Cl

diisopropylethylamine

1,6-hexanediol

→

37

Ausbeute 33.3%

O-(4,4' -dimethoxytrityl)-1,6-hexanediol

Ausbeute 33.3%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture was quenched with 85 mL of 5% sodium bicarbonate
2. 2
   Extraktionextracted with 2×100 mL of methylene chloride
3. 3
   WaschenThe organic phase was washed with 2×100 mL of water and 100 mL of brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by flash chromatography (3.5×17 cm silica)
8. 8
   workup.ADDITIONThe fractions containing pure product
9. 9
   Einengenconcentrated

Vorschrift

To a solution of 3.38 g (10 mmol) of DMTr-Cl and 3.45 mL (20 mmol) of diisopropylethylamine in 50 mL of dry pyridine was added 5.91 g (50 mmol) of 1,6-hexanediol. After stirring for 4 h, the mixture was quenched with 85 mL of 5% sodium bicarbonate and extracted with 2×100 mL of methylene chloride. The organic phase was washed with 2×100 mL of water and 100 mL of brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (3.5×17 cm silica) using methylene chloride. The fractions containing pure product were combined and concentrated to give 1.40 g of 37 as a yellow syrup.

Quelle