Tridecanoic acid → Methyl 4-tridecanoylpyrrole-2-carboxylate

HRID 129340

Reaction equation

HRID 129340 reaction equation
[C:1](O)(=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[NH:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[C:29]([O:31][CH3:32])=[O:30]>C(Cl)Cl.CN(C)C=O>[C:1]([C:27]1[CH:26]=[C:25]([C:29]([O:31][CH3:32])=[O:30])[NH:24][CH:28]=1)(=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 12530Tridecanoic acidHCID 24386Thionyl ChlorideHCID 136930Methyl pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15023257Methyl 4-tridecanoylpyrrole-2-carboxylateYield 83.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent4×

Procedure

Tridecanoic acid (102.8 g, 0.48 mol) was dissolved into 480 ml of methylene chloride, and 52.6 ml (0.72 mol) of thionyl chloride and 0.2 ml of N,N-dimethylformamide were added thereto. The mixture was allowed to stand overnight followed by concentration under reduced pressure, and the remaining oil was added to 400 ml of methylene chloride containing 106.6 g (0.8 mol) of anhydrous aluminium chloride. A solution of 50.05 g (0.4 mol) of methyl pyrrole-2-carboxylate in 200 ml of methylene chloride was added dropwise to the mixture for ca. 40 minutes at 3° to 9° C. After the addition was finished, the temperature was raised gradually to room temperature, and the mixture was stirred for 2 hours followed by pouring it into 800 ml of ice water. To this mixture was added 1000 ml of methylene chloride to completely dissolve the crystals. The organic layer was separated, washed with water three times and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was recrystallized from 400 ml of ethyl acetate and 400 ml of hexane to give 107.2 g (83% yield) of methyl 4-tridecanoylpyrrole-2-carboxylate as white crystals, m.p. 92°-93° C.

Workup

  1. additionwere added
  2. concentrationfollowed by concentration under reduced pressure
  3. additionAfter the addition
  4. dissolutionto completely dissolve the crystals
  5. customThe organic layer was separated
  6. washwashed with water three times
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationAfter concentration under reduced pressure
  9. customthe residue was recrystallized from 400 ml of ethyl acetate and 400 ml of hexane

Sources & evidence

ORD record
ord-4f8ef37fdafc467c89be2805860ca5f1
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Linked notes

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