Reaktion #2244

Reaktionsgleichung

2-[2-(2-hydroxyphenyl)vinyl]-1-methylindole

triphenylphosphine

diethylazodicarboxylate

THF

→

(S)-2-{2[2-(1-methoxycarbonylethoxy)phenyl]vinyl}-1-methylindole

Ausbeute 90.0%

Lösungsmittel

Brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled condition
2. 2
   Extraktionfollowed by extraction with methylene chloride
3. 3
   TrocknenThe extract was dried over Na2SO4
4. 4
   Sonstigeevaporated
5. 5
   workup.ADDITIONCHCl3 -n-hexane was added to the residue
6. 6
   Filtrationafter filtration
7. 7
   Sonstigethe organic layer was purified by silica gel column chromatography (CHCl3 /n-hexane/AcOEt=10/10/1)

Vorschrift

To a solution of 1.50 g (6.02 mmol) of 2-[2-(2-hydroxyphenyl)vinyl]-1-methylindole, 1.89 g (7.21 mmol) of triphenylphosphine and 0.69 ml (7.22 mmol) of R-(+)-methyl lactate in 15 ml of THF was added 1.14 ml (7.24 mmol) of diethylazodicarboxylate under an ice-cooled condition, followed by stirring at room temperature for 2 hours. Brine was added to the reaction mixture, followed by extraction with methylene chloride. The extract was dried over Na2SO4, and evaporated. CHCl3 -n-hexane was added to the residue and, after filtration, the organic layer was purified by silica gel column chromatography (CHCl3 /n-hexane/AcOEt=10/10/1) to give 1.82 g (90%) of (S)-2-{2[2-(1-methoxycarbonylethoxy)phenyl]vinyl}-1-methylindole.

Quelle