Reaktion #1111301

Reaktionsgleichung

THF

45

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

K2CO3

HCl

→

title compound

Ausbeute 75.0%

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

Ausbeute 75.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction was stirred further for 1.5 h
2. 2
   ExtraktionThe mixture was extracted with ethyl acetate (2×20 mL)
3. 3
   Trocknenthe combined solution was dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigePurification of the residue by flash chromatography

Vorschrift

A mixture of 45 (40 mg, 0.069 mmol), K2CO3 (10 mg, 0.072 mmol) in methanol (0.5 mL) was stirred at room temperature. After 1 h, the diester had not dissolved and so 0.2 mL THF was added. The reaction was stirred further for 1.5 h and then 10 mL 1 M HCl was added. The mixture was extracted with ethyl acetate (2×20 mL) and the combined solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography using a Combiflash unit by Teledyne Isco (12 g silica gel, 0%→20% ethyl acetate/hexanes) gave the title compound (22 mg, 0.051 mmol, 75%).

Quelle