Ethyl Acetate → HCID 13220943, compound

HRID 1719882Notes

Reaction equation

HRID 1719882 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[NH:11][CH:12]=[CH:13][CH:14]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O1CCCC1>[CH2:8]([C:10]1[NH:11][CH:12]=[CH:13][CH:14]=1)[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 134470562-Phenyl-1-(1H-pyrrol-2-yl)ethan-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 13220943HCID 13220943, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.00 g (0.032 mole) of the 2-phenylacetylpyrrole (III) in 200 ml of anhydrous tetrahydrofuran was added to a suspension of 600 g (0.153 mole) of lithium aluminum hydride in dry tetrahydrofuran. The mixture was stirred at reflux temperature for 48 h. The mixture was cooled to 0°, ethyl acetate was cautiously added to destroy the excess hydride and then saturated aqueous sodium sulfate was added. The organic phase was decanted, dried over sodium sulfate and evaporated in vacuo. The residue was subjected to column chromatography on neutral alumina (Fluka, Act II). 4.800 g (88%) of 2-[phenethyl]pyrrole (IV) was eluted with hexane-ethyl acetate and crystallized, m.p. 40°-42° (hexane). (Step 2).

Workup

  1. temperatureat reflux temperature for 48 h
  2. temperatureThe mixture was cooled to 0°
  3. customto destroy the excess hydride
  4. additionsaturated aqueous sodium sulfate was added
  5. customThe organic phase was decanted
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. wash4.800 g (88%) of 2-[phenethyl]pyrrole (IV) was eluted with hexane-ethyl acetate
  9. customcrystallized

Sources & evidence

ORD record
ord-5a16cb4cd35548128f009a61810779a0
Source dataset
uspto-grants-1985_09
Patent number
US04543361

Reaction notes

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