Reaktion #1111298

Reaktionsgleichung

TBAF

42b

5-[3-((S)-2-{4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-hexyl]-phenyl}-cyclopent-2-enyl)-propyl]-thiophene-2-carboxylic acid methyl ester

→

title compound

Ausbeute 73.5%

5-(3-{(S)-2-[4-((S)-1-Hydroxy-hexyl)-phenyl]-cyclopent-2-enyl}-propyl)-thiophene-2-carboxylic acid methyl ester

Ausbeute 73.5%

Lösungsmittel

NH4Cl

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with ethyl acetate (2×20 mL)
2. 2
   TrocknenThe combined ethyl acetate solution was dried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Sonstigeevaporated
5. 5
   SonstigePurification of the residue by flash chromatography

Vorschrift

TBAF (0.4 mL, 0.4 mmol, 1 M/THF) was added to 42b (45 mg, 0.083 mmol) and the resulting solution was allowed to stir for 4 h. Saturated NH4Cl (20 mL) solution was added and the mixture was extracted with ethyl acetate (2×20 mL). The combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography using a Combiflash unit by Teledyne Isco (330 g silica gel, 0%→20% ethyl acetate/hexanes) gave the title compound (26 mg, 0.061 mmol, 73%).

Quelle