Sodium hydride → methyl 4-(3-methylbutanoyl)-1H-pyrrole-3-carboxylate

HRID 1835132Notes

Reaction equation

HRID 1835132 reaction equation
[CH3:1][CH:2]([CH3:12])[CH2:3][C:4](=[O:11])/[CH:5]=[CH:6]/[C:7]([O:9][CH3:10])=[O:8].C1(C)C=CC(S([CH2:22][N+:23]#[C-:24])(=O)=O)=CC=1.[H-].[Na+].[Cl-].[NH4+]>C(OCC)C.CS(C)=O>[CH3:1][CH:2]([CH3:12])[CH2:3][C:4]([C:5]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:22][NH:23][CH:24]=1)=[O:11]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 161915Tosylmethyl isocyanideHCID 12683158(e)-Methyl 6-methyl-4-oxo-2-heptenoate

Product 1

HCID 5282540methyl 4-(3-methylbutanoyl)-1H-pyrrole-3-carboxylateYield 26.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of (E)-methyl 6-methyl-4-oxo-2-heptenoate (10 g) prepared as described in a) above and (para-toluenesulfonyl)methyl isocyanide (11.5 g) in a mixture of dry dimethyl sulfoxide (30 ml) and diethyl ether (30 ml) was added over one hour to sodium hydride (2.75 g of a 60% oil dispersion, 0.068 mol) stirred in dry diethyl ether (90 ml) under nitrogen. After a further hour saturated ammonium chloride solution was added and the mixture was extracted with ethyl acetate, which was washed well with water, dried, and evaporated to a gum. The gum was chromatographed with ethyl acetate-isohexane (2:3) to afford a solid (3.3 g) which was crystallised from ethyl acetate-cyclohexane to give the sub-title ester.

Workup

  1. extractionthe mixture was extracted with ethyl acetate, which
  2. washwas washed well with water
  3. customdried
  4. customevaporated to a gum
  5. customThe gum was chromatographed with ethyl acetate-isohexane (2:3)

Sources & evidence

ORD record
ord-9289214be66f4cd58b328a5e689a35d5
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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