Tetrahydrofuran → HCID 10797882, compound
Reaction equation
C(OCC[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)C.[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]=1Participants
Procedure
1-(3-thienyl)phenylethyl 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 layers 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, 7g).
Workup
- additionwas added carefully
- dry with materialto dry liquid ammonia (300 ml)
- additionLithium metal was added in small portions until the blue color
- customThe resulting reaction mixture
- customthe reaction was quenched by addition of solid ammonium chloride
- customThe residue, after the complete evaporation of liquid ammonia
- dissolutionwas dissolved in water (100 ml)
- extractionwas extracted with methylene chloride (4×50 ml)
- dry with materialThe combined organic layers was dried over MgSO4
- filtrationfiltered
- customRemoval of the solvent
- customgave a crude product, which
- customwas purified by column chromatography
- additionfollowed by mixture of ethyl acetate in hexane as eluent
Sources & evidence
- ORD record
- ord-2c25e943b15c478f80f335067d2404f9
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05594021
Reaction notes
Loading…