Ethyl-4-phenyl-3-furoate → (4-Phenylfuran-3-yl)methanol

HRID 1736522Notes

Reaction equation

HRID 1736522 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][O:14][CH:13]=1)=O)C>O1CCCC1>[C:17]1([C:16]2[C:12]([CH2:10][OH:9])=[CH:13][O:14][CH:15]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 15037153Ethyl-4-phenyl-3-furoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15037154(4-Phenylfuran-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (1.0M solution in hexane 1.14 ml, 1.14 mmol) was added dropwise to a solution of ethyl-4-phenyl-3-furoate (246 mg, assumed 1.28 mmol) in tetrahydrofuran (20 ml) at 0 degrees under argon. The solution was stirred and was allowed to warm to room temperature gradually over 1/2 hour. The mixture was quenched with saturated ammonium chloride and the organics were extracted into ethyl ether, and washed with H2O . Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromatography on silica using 20% ethyl acetate/hexanes. This was further purified by recrystallation (hexane/ethyl ether) to give the title compound as pale yellow crystals.

Workup

  1. customThe mixture was quenched with saturated ammonium chloride
  2. extractionthe organics were extracted into ethyl ether
  3. washwashed with H2O
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave an oil, which
  7. customwas purified by flash chromatography on silica using 20% ethyl acetate/hexanes
  8. customThis was further purified by recrystallation (hexane/ethyl ether)

Sources & evidence

ORD record
ord-2c8172e3ee4545e2bd8998bc43311047
Source dataset
uspto-grants-1996_07
Patent number
US05541221

Reaction notes

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