Reaktion #2289133

Reaktionsgleichung

dibromide

5-[3-((1S,2S)-3,3-Dibromo-2-{4-[1-(4-methoxy-benzyloxy)-hexyl]-phenyl}-cyclopentyl)-propyl]-thiophene-2-carboxylic acid methyl ester

2-tert-butyl-1,1,3,3-tetramethylguanidine

HCl

→

alkene

Ausbeute 15.0%

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

Ausbeute 15.0%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with CH2Cl2 (3×25 mL)
2. 2
   TrocknenThe combined dichloromethane solution was dried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Sonstigeevaporated
5. 5
   SonstigePurification by flash chromatography (0%→20% ethyl acetate/hexanes)

Vorschrift

A solution of dibromide 3 (52 mg, 0.074 mmol) and 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG, 0.8 mL) in 1,2-dichloroethane (2 mL) was stirred at room temperature. After 3 days, 1 M HCl was added and the mixture was extracted with CH2Cl2 (3×25 mL). The combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (0%→20% ethyl acetate/hexanes) gave the title compound contaminated with 15% of the alkene regioisomer 5b as an inseparable mixture (45 mg, 97%).

Quelle