Tetrahydrofuran → HCID 10797882, compound

HRID 1899721Notes

Reaction equation

HRID 1899721 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH2:8]1)(=[O:3])[CH3:2].[CH2:18]1COC[CH2:19]1>>[CH2:7]([C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[CH2:12][C:11]1[CH:10]=[CH:9][CH:8]=[CH:19][CH:18]=1.[C:1]([O:4][CH2:5][CH2:6][C:7]1([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH2:12]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 69946342HCID 69946342, compound

Product 2

HCID 10797882HCID 10797882, compoundYield 34%HCID 69946342HCID 69946342, compound

Procedure

1-(3-thienyl)phenethyl acetate dissolved in THF (20 ml) was added carefully to dry liquid ammonia (300 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 the complete evaporation of liquid ammonia, was dissolved in water (100 ml) and was extracted with methylene chloride (4×50 ml). The combined organic layer was dried over MgSO4 and filtered. Removal of the solvent gave a crude product, which was purified by column chromatography using hexane followed by mixture of ethyl acetate in hexane as eluent to give 3-phenethylthiophene (3.2 g, 34% yield) and 1-(3-thienyl)phenethyl acetate (starting material, 7 g).

Workup

  1. additionwas added carefully
  2. dry with materialto dry liquid ammonia (300 ml)
  3. additionLithium metal was added in small portions until the blue color
  4. customThe resulting reaction mixture
  5. customthe reaction was quenched by addition of solid ammonium chloride
  6. customThe residue, after the complete evaporation of liquid ammonia
  7. dissolutionwas dissolved in water (100 ml)
  8. extractionwas extracted with methylene chloride (4×50 ml)
  9. dry with materialThe combined organic layer was dried over MgSO4
  10. filtrationfiltered
  11. customRemoval of the solvent
  12. customgave a crude product, which
  13. customwas purified by column chromatography
  14. additionfollowed by mixture of ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-fb21f6005bac468e83567491fe1dff0c
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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