Tetrahydrofuran → Methyl 4-(1-cis tridecenyl)pyrrole-2-carboxylate

HRID 129344Notes

Reaction equation

HRID 129344 reaction equation
C([Li])CCC.O1CCCC1.[Br-].[CH2:12]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[CH:43]([C:45]1[CH:46]=[C:47]([C:50]([O:52][CH3:53])=[O:51])[NH:48][CH:49]=1)=O>CCCCCC.O>[CH:43](/[C:45]1[CH:46]=[C:47]([C:50]([O:52][CH3:53])=[O:51])[NH:48][CH:49]=1)=[CH:23]/[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 84955Dodecyltriphenylphosphonium bromideHCID 640310methyl 4-formyl-1H-pyrrole-2-carboxylateHCID 178418339Butyllithium

Product 1

HCID 15023334Methyl 4-(1-cis tridecenyl)pyrrole-2-carboxylateYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

A ca. 15% solution (18.5 ml) of n-butyllithium in hexane was added dropwise at -50° C. to a tetrahydrofuran suspension (95 ml) of 16.0 g (31.4 mmol) of dodecyltriphenylphosphonium bromide described in Chemistry and Industry (London) p. 1086, 1958. The temperature was raised to room temperature and the mixture was stirred for 30 minutes. The temperature was again lowered to -50° C. To the mixture was added dropwise a tetrahydrofuran solution (50 ml) of 2.4 g (15.7 mmol) of methyl 4-formylpyrrole-2-carboxylate described in Bulletin de la Societe Chimique de France, p. 283, 1972. The mixture was stirred for 1 hour, diluted with water, extracted with ethyl acetate, washed with an aqueous saturated solution of sodium chloride 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=1/7) to obtain 3.11 g (65% yield) of methyl 4-(1-cis tridecenyl)pyrrole-2-carboxylate, m.p. 51°-52° C.

Workup

  1. customwas again lowered to -50° C
  2. stirringThe mixture was stirred for 1 hour
  3. extractionextracted with ethyl acetate
  4. washwashed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removing the solvent under reduced pressure
  7. customthe residue was purified

Sources & evidence

ORD record
ord-b3178c436b744eec97f807fde774d867
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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