Reaktion #40847

Reaktionsgleichung

deoxybenzoin

NaOEt

ethyl formate

→

title compound

(Z)-3-Hydroxy-2,3-diphenyl-propenal

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITplaced in the refrigerator for 4 days
2. 2
   workup.STIRRINGAfter the mixture was stirred overnight at room temperature
3. 3
   Extraktionextracted with CH2Cl2
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over MgSO4 anhydride
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by column chromatography (10% ethyl acetate in hexane)

Vorschrift

To a cooled solution of NaOEt (763 mg, 11.21 mmol) in EtOH (100 ml) was added ethyl formate (0.91 ml, 11.21 mmol) dropwise. The resulting mixture is allowed to stand for 3 hours at 0 to 5° C., and then deoxybenzoin (2 g, 10.19 mmol) was added. The mixture was stirred for 2 hours at 0 to 5° C. and then placed in the refrigerator for 4 days. After the mixture was stirred overnight at room temperature, it was poured into ice-water, and acidified, and extracted with CH2Cl2. The organic layer was washed with brine, and dried over MgSO4 anhydride, and concentrated in vacuo. The residue was purified by column chromatography (10% ethyl acetate in hexane) to give the title compound as a light yellow solid.

Quelle