Water → 2-Methyl-3-(1H-pyrrol-1-yl)benzenemethanol

HRID 1759204Notes

Reaction equation

HRID 1759204 reaction equation
[CH3:1][C:2]1[C:10]([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(OCC)C.O>O1CCCC1>[CH3:1][C:2]1[C:10]([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 962Water2×HCID 3283Diethyl EtherHCID 7711292-Methyl-3-pyrrol-1-yl-benzoic acid

Product 1

HCID 155817552-Methyl-3-(1H-pyrrol-1-yl)benzenemethanolYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 7.5 grams (0.037 mole) of 2-methyl-3-(pyrrol-1-yl)benzoic acid in 125 ml of tetrahydrofuran was added dropwise 4.8 grams (0.056 mole) of a borane-tetrahydrofuran complex. The addition required 30 minutes. Upon complete addition the reaction mixture was heated under reflux for 2.5 hours then cooled slowly. To the cooled reaction mixture was carefully added 150 ml of diethyl ether previously saturated with water, followed by 50 ml of water. The mixture was poured into a separatory funnel and washed with 100 ml of aqueous 2 N sodium hydroxide. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 6.8 grams of 2-methyl-3-(pyrrol-1-yl)phenylmethanol as an oil.

Workup

  1. additionThe addition required 30 minutes
  2. additionUpon complete addition the reaction mixture
  3. temperaturewas heated
  4. temperatureunder reflux for 2.5 hours
  5. temperaturethen cooled slowly
  6. customTo the cooled reaction mixture
  7. additionThe mixture was poured into a separatory funnel
  8. washwashed with 100 ml of aqueous 2 N sodium hydroxide
  9. dry with materialThe organic layer was dried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4d4bd6ac34f6430b87c0d7bae2940ebe
Source dataset
uspto-grants-1982_07
Patent number
US04339457

Reaction notes

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