Hydrochloric Acid → HCID 53942021, compound

HRID 129334Notes

Reaction equation

HRID 129334 reaction equation
[BH4-].[Na+].[C:3]([C:19]1[NH:23][CH:22]=[C:21]([C:24]([O:26]CC)=[O:25])[CH:20]=1)(=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[OH-].[K+].Cl>C(O)C.O>[CH:3]([C:19]1[NH:23][CH:22]=[C:21]([C:24]([OH:26])=[O:25])[CH:20]=1)=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 15023380HCID 15023380, compound

Product 1

HCID 53942021HCID 53942021, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium borohydride (500 mg, 13 mmol) was added to an ethanol solution (100 ml) of 4.59 g (13 mmol) of ethyl 5-pentadecanoylpyrrole-3-carboxylate prepared in the same manner as in Synthetic Example 4. The mixture was stirred at room temperature for 16 hours. After a removal of the ethanol under reduced pressure, the mixture was treated with water, extracted with ether, washed with water and dried over anhydrous magnesium sulfate. A removal of the solvent under reduced pressure quantitatively gave an alcoholic compound. To the resulting product were added 3.53 g (63 mmol) of potassium hydroxide in ethanol (35 ml) and water (12 ml), and the mixture was heated under reflux for 5 days. The resulting mixture was acidified with 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 residue was purified by subjecting it to column chromatography over silica gel (eluent: ethyl acetate/hexane=1/2) to obtain 2.33 g (60 % yield) of 5-(1-pentadecenyl)pyrrole-3-carboxylic acid, m.p. 90°-96° C.

Workup

  1. customprepared in the same manner as in Synthetic Example 4
  2. customAfter a removal of the ethanol under reduced pressure
  3. additionthe mixture was treated with water
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customA removal of the solvent under reduced pressure
  8. customquantitatively gave an alcoholic compound
  9. temperaturethe mixture was heated
  10. temperatureunder reflux for 5 days
  11. extractionextracted with ethyl acetate
  12. washThe extract was washed with water
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customAfter removing the solvent under reduced pressure
  15. customthe residue was purified

Sources & evidence

ORD record
ord-0d1f84524e624d699d365f1bc1890601
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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