Pyrrole-3-carboxylic acid → tert-butyl 1H-pyrrole-3-carboxylate

HRID 1821930Notes

Reaction equation

HRID 1821930 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1>C1C=CC=CC=1.C(OCC)C>[C:3]([O:7][C:6]([C:3]1[CH:4]=[CH:5][NH:1][CH:2]=1)=[O:8])([CH3:6])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 101030Pyrrole-3-carboxylic acid

Product 1

HCID 11171190tert-butyl 1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

0.50 g (4.50 mmol) pyrrole-3-carboxylic acid is suspended in 15 ml absolute benzene and boiled under reflux. A solution 4.07 g (18.0 mmol) 90% N,N-dimethylformamidedi-tert-butylacetal in 15 ml absolute benzene is added drop-wise within 30 min. Following another heating under reflux for 30 minutes and subsequent cooling, the reaction mixture is diluted with diethyl ether, washed with 5% sodium carbonate solution and saturated NaCl solution. Drying on sodium sulfate, filtration and concentration on the rotary evaporator leave as a crude product a yellow solid which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 90:10) and yields the product as a white solid.

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux for 30 minutes
  3. washwashed with 5% sodium carbonate solution and saturated NaCl solution
  4. customDrying on sodium sulfate, filtration and concentration on the rotary evaporator
  5. customleave as a crude product a yellow solid which
  6. customis purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 90:10)

Sources & evidence

ORD record
ord-64cc34cca8b4475bbcc75cc4b9ed6660
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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