Formaldehyde → 3-Benzyl-1-pyrrolylmethanol

HRID 2057782Notes

Reaction equation

HRID 2057782 reaction equation
[CH2:1]([C:8]1[CH:12]=[CH:11][NH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]=[O:14]>C(=O)([O-])[O-].[K+].[K+].O1CCCC1>[CH2:1]([C:8]1[CH:12]=[CH:11][NH:10][C:9]=1[CH2:13][OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 117688281H-Pyrrole, 3-(phenylmethyl)-

Product 1

HCID 543430813-Benzyl-1-pyrrolylmethanolYield 97.3%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2.18 g (13.9 mmole) of 3-benzylpyrrole, 0.42 g (13.9 mmole) of paraformaldehyde and 0.07 g (0.5 mmole) of anhydrous potassium carbonate are mixed and stirred at 50° C. for 4 hours in an atmosphere of nitrogen. Dry tetrahydrofuran is added to the reaction solution and filtered. The filtrate is concentrated to obtain 2.53 g of 3-benzyl-1-pyrrolylmethanol as a pale yellow liquid. Yield 97.3%. nD31.5 1.5837.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-b99dbed25c0b466dac8cf169157b38b5
Source dataset
uspto-grants-1980_07
Patent number
US04212879

Reaction notes

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