Sodium Sulfate → (4-phenyl-1H-pyrrol-2-yl)methanol

HRID 880444Notes

Reaction equation

HRID 880444 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:12](OCC)=[O:13])[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:1]1([C:7]2[CH:8]=[C:9]([CH2:12][OH:13])[NH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 14643813Ethyl 4-phenyl-1H-pyrrole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 67238716(4-phenyl-1H-pyrrol-2-yl)methanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 4-phenyl-1H-pyrrole-2-carboxylate (1 g, 5.58 mmol) in tetrahydrofuran (10 mL) was added to a suspension of lithium aluminum hydride (300 mg, 8.10 mmol) in tetrahydrofuran (20 mL) at 0° C. The reaction mixture was slowly warmed to ambient temperature and stirred for 5 h. The mixture was slowly added to saturated sodium sulphate followed by extraction with ethyl acetate (2×25 mL). The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford (4-phenyl-1H-pyrrol-2-yl)methanol (800 mg, 84%) as a solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate (2×25 mL)
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f74aec3b02704fb7b7a11ad809d79ffa
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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