Reaktion #87910

Reaktionsgleichung

tBuOH

TFAA

215-11-COOH

10-(3-Chloro-5-formyl-2,6-dihydroxy-4-methylphenyl)decanoic acid

NaHCO3

→

product

Ausbeute 17.0%

tert-Butyl 10-(3-chloro-2,6-dihydroxy-5-formyl-4-methylphenyl)decanoate

Ausbeute 17.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the cooled mixture, which
2. 2
   Temperaturto warm to room temperature
3. 3
   workup.STIRRINGwith stirring for 15 hours
4. 4
   Extraktionwas extracted with EtOAc twice
5. 5
   workup.STIRRINGafter stirring for 5 minutes
6. 6
   WaschenThe combined organic layer was washed with a saturated aqueous NaCl solution
7. 7
   Trocknenwas dried over anhydrous Na2SO4
8. 8
   SonstigeAfter evaporation of the solvent
9. 9
   Sonstigethe residue was purified by column chromatography on silica gel (Hexane:EtOAc=7:1 to 4:1)

Vorschrift

TFAA (0.20 ml, 1.4 mmol) was added to a suspension of Compound 215-11-COOH (144 mg, 0.403 mmol) in toluene (5 ml) at 0° C., and the mixture was allowed to warm to room temperature with stirring for 30 minutes. After checking for complete dissolution of the raw material, the mixture was again cooled to 0° C. tBuOH (0.40 ml, 4.2 mmol) was added to the cooled mixture, which was allowed to warm to room temperature with stirring for 15 hours. A saturated aqueous NaHCO3 solution was added to the reaction solution, which was extracted with EtOAc twice after stirring for 5 minutes. The combined organic layer was washed with a saturated aqueous NaCl solution, and was dried over anhydrous Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc=7:1 to 4:1) followed by PTLC (Hexane:EtOAc=7:1) to yield the target product (28 mg, 17%).

Quelle