반응 #1111287

반응 방정식

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

수율 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

수율 15.0%

용매

1,2-dichloroethane

반응 조건

후처리

1. 1
   추출the mixture was extracted with CH2Cl2 (3×25 mL)
2. 2
   건조The combined dichloromethane solution was dried (Na2SO4)
3. 3
   여과filtered
4. 4
   기타evaporated
5. 5
   기타Purification by flash chromatography (0%→20% ethyl acetate/hexanes)

실험 절차

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%).

출처