Tetrahydrofuran → Thiophene, 2-(phenylmethyl)-

HRID 1166871노트

반응식

HRID 1166871 반응식
C(OC[C:6]1([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH2:7]1)(=O)C.[CH2:17]1COCC1>>[CH2:6]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:11]1[CH:17]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

3

반응물 2

HCID 8028TetrahydrofuranHCID 69948862HCID 69948862, 화합물

생성물 1

HCID 139391Thiophene, 2-(phenylmethyl)-수율 68%

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).

후처리

  1. dry with materialto dry liquid ammonia (100 ml)
  2. additionLithium metal was added in small portions until the blue color
  3. customThe resulting reaction mixture
  4. customthe reaction was quenched by addition of solid ammonium chloride
  5. customThe residue, after complete evaporation of liquid ammonia
  6. dissolutionwas dissolved in water (50 ml)
  7. extractionwas extracted with methylene chloride (2×50 ml)
  8. dry with materialThe combined organic layers was dried over MgSO4
  9. filtrationfiltered
  10. customRemoval of the solvent
  11. customgave crude product, which
  12. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-a7dab13d83e94732aebe20ed14c6f6d2
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613804B2

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