Tetrahydrofuran → Thiophene, 2-(phenylmethyl)-

HRID 1166871Notes

Reaction equation

HRID 1166871 reaction equation
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

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 69948862HCID 69948862, compound

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a7dab13d83e94732aebe20ed14c6f6d2
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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