Reaktion #92087

Reaktionsgleichung

butyraldehyde

AcOH

(+)-γ-tocopherol

AcOH

EtOAc

→

7,9,10-trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene

Ausbeute 100.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with DCM (3×20 mL)
2. 2
   WaschenThe combined organic layers were washed with water (3×15 mL)
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated by rotary evaporation

Vorschrift

A 25 mL RBF was charged with butyraldehyde (155 mg, 2.16 mmol), AcOH (2 mL) and H2SO4 (1 drop). To the flask was then added a solution of (+)-γ-tocopherol (Ex-1C-1) (300 mg, 0.72 mmol) in AcOH (3 mL) dropwise over 2 h via syringe pump. The reaction was then stirred for 16 h and monitored by TLC (9:1 Hept:EtOAc). The reaction was then diluted with water (15 mL) and extracted with DCM (3×20 mL). The combined organic layers were washed with water (3×15 mL), dried over Na2SO4, filtered and concentrated by rotary evaporation to yield 7,9,10-trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene (Ex-1C-2) as a brownish oil (425 mg, >100%), which was used without further purification.

Quelle