반응 #321542

반응 방정식

1-(2-thienyl)benzyl acetate

THF

→

2-benzylthiophene

수율 68.0%

반응 조건

후처리

1. 1
   건조to dry liquid ammonia (100 ml)
2. 2
   workup.ADDITIONLithium metal was added in small portions until the blue color
3. 3
   기타The resulting reaction mixture
4. 4
   기타the reaction was quenched by addition of solid ammonium chloride
5. 5
   기타The residue, after complete evaporation of liquid ammonia
6. 6
   workup.DISSOLUTIONwas dissolved in water (50 ml)
7. 7
   추출was extracted with methylene chloride (2×50 ml)
8. 8
   건조The combined organic layers was dried over MgSO4
9. 9
   여과filtered
10. 10
    기타Removal of the solvent
11. 11
    기타gave crude product, which
12. 12
    기타was purified by column chromatography

실험 절차

A solution of 1-(2-thienyl)benzyl acetate in THF (5 ml) was added carefully to dry liquid ammonia (100 ml). Lithium metal was added in small portions until the blue color persisted. The resulting reaction mixture was stirred for 30 min, and the reaction was quenched by addition of solid ammonium chloride. The residue, after complete evaporation of liquid ammonia, was dissolved in water (50 ml) and was extracted with methylene chloride (2×50 ml). The combined organic layers was dried over MgSO4 and filtered. Removal of the solvent gave crude product, which was purified by column chromatography using hexane as eluent to give 2-benzylthiophene (1.2 g, 68% yield).

출처