Hydrochloric Acid → Methyl 4-tetradecanoylpyrrole-2-carboxylate

HRID 1090737Notes

Reaction equation

HRID 1090737 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[C:10](Cl)(=[O:24])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].Cl>C1C=CC=CC=1>[C:10]([C:4]1[CH:3]=[C:2]([C:6]([O:8][CH3:9])=[O:7])[NH:1][CH:5]=1)(=[O:24])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66986Myristoyl chlorideHCID 136930Methyl pyrrole-2-carboxylate

Product 1

HCID 15023256Methyl 4-tetradecanoylpyrrole-2-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution (5 ml) of 1.25 g (10 mmol) of methyl pyrrole-2-carboxylate in benzene was added 2.71 g (11 mmol) of tetradecanoyl chloride under ice-cooling, followed by adding 1.73 ml (15 mmol) of stannic chloride dropwise thereto. The mixture was stirred for 2 hours at room temperature, treated with diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the product was purified by subjecting it to column chromatography over silica gel (ethyl acetate/hexane=1/7) to obtain 1.80 g (54% yield) of methyl 4-tetradecanoylpyrrole-2-carboxylate.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing the solvent under reduced pressure
  6. customthe product was purified

Sources & evidence

ORD record
ord-601d55c6fff34bf88b418445dd3624aa
Source dataset
uspto-grants-1992_01
Patent number
US05082856

Reaction notes

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