Water → [3-(1H-Pyrrol-1-yl)phenyl]methanol

HRID 1759202Notes

Reaction equation

HRID 1759202 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:12]2[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=2)[C:15](OCC)=[O:16])[CH:11]=[CH:10][CH:9]=[CH:8]1.O.O1CCCC1.O>C(OCC)C>[N:7]1([C:12]2[CH:13]=[C:14]([CH2:15][OH:16])[CH:20]=[CH:21][CH:22]=2)[CH:11]=[CH:10][CH:9]=[CH:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 47637241-(3-Ethoxycarbonylphenyl)pyrroleHCID 21226445Aluminium lithium hydride2×HCID 21881883Oxolane--water (1/1)

Product 1

HCID 2776531[3-(1H-Pyrrol-1-yl)phenyl]methanolYield 111.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred mixture of 4.8 grams of lithium aluminum hydride in 150 ml of dry diethyl ether was added dropwise 23.2 grams (0.108 mole) of ethyl 3-(pyrrol-1-yl)benzoate in 160 ml of dry diethyl ether. The complete addition required 45 minutes. After this time the reaction mixture was heated under reflux for 45 minutes then allowed to cool to ambient temperature where it stood for 16 hours. The excess lithium aluminum hydride was decomposed by the careful addition of 20 ml of 50% (v/v) water-tetrahydrofuran. The addition required 20 minutes as the reaction mixture temperature was kept below 25° C. The reaction mixture was poured into 300 ml of water and the diethyl ether layer separated. The aqueous layer was extracted with three portions of 200 ml each of diethyl ether. The combined ether layers were washed with water and dried with magnesium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure to give 20.9 grams of 3-(pyrrol- 1-yl)phenylmethanol; mp 64°-67° C. The ir spectrum was consistent with the proposed structure.

Workup

  1. additionThe complete addition required 45 minutes
  2. temperatureAfter this time the reaction mixture was heated
  3. temperatureunder reflux for 45 minutes
  4. additionThe addition required 20 minutes as the reaction mixture temperature
  5. customwas kept below 25° C
  6. customthe diethyl ether layer separated
  7. extractionThe aqueous layer was extracted with three portions of 200 ml each of diethyl ether
  8. washThe combined ether layers were washed with water
  9. dry with materialdried with magnesium sulfate
  10. filtrationThe mixture was filtered
  11. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-70b7a0ef381e4083b833887a9f009ef8
Source dataset
uspto-grants-1982_07
Patent number
US04339457

Reaction notes

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