Hydrochloric Acid → Methyl 4-(3-methyl-1-oxobutyl)-1-(1-naphthalenylmethyl)-1H-pyrrole-3-carboxylate

HRID 1835133Notes

Reaction equation

HRID 1835133 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH3:17])[CH2:5][C:6]([C:8]1[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][NH:11][CH:12]=1)=[O:7].[C:18]1([CH2:28]Cl)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.Cl>CN(C)C=O.[I-].[K+]>[CH3:3][CH:4]([CH3:17])[CH2:5][C:6]([C:8]1[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][N:11]([CH2:28][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[CH:12]=1)=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 68451-ChloromethylnaphthaleneHCID 24758Sodium hydrideHCID 5282540methyl 4-(3-methylbutanoyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 5282541Methyl 4-(3-methyl-1-oxobutyl)-1-(1-naphthalenylmethyl)-1H-pyrrole-3-carboxylateYield 71%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To sodium hydride (0.42 g of a 60% oil dispersion, 0.0105 mol), freed from oil, stirred in dry dimethyl formamide (15 ml) under nitrogen was added methyl 4-(3-methyl-1-oxobutyl)-1H-pyrrole-3-carboxylate (2.2 g) prepared as described in b) above in portions over 20 minutes. After 10 minutes, potassium iodide (0.01 g) and (1-naphthalenyl)methyl chloride (1.85 g) in dimethyl formamide (20 ml) were added. The mixture was stirred for 4 hours and then poured into 0.5M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed well with water and then brine, dried and evaporated to a gum, which was chromatographed with ethyl acetate-isohexane (1:3) to give an oil. The oil was crystallised from cyclohexane to yield the subtitle pyrrole (2.6 g).

Workup

  1. customprepared
  2. customover 20 minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed well with water
  5. dry with materialbrine, dried
  6. customevaporated to a gum, which
  7. customwas chromatographed with ethyl acetate-isohexane (1:3)
  8. customto give an oil
  9. customThe oil was crystallised from cyclohexane

Sources & evidence

ORD record
ord-27fca605ca0f4bd4b142125fef149922
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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