Dimethylformamide → Methyl 3-formyl-4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate

HRID 1582324Notes

Reaction equation

HRID 1582324 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][C:12]1[CH:13]=[C:14]([C:23]([O:25][CH3:26])=[O:24])[N:15]([CH2:18][C@H:19]2[CH2:21][C@@H:20]2[CH3:22])[C:16]=1[CH3:17].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O>[CH:8]([C:13]1[C:12]([CH3:11])=[C:16]([CH3:17])[N:15]([CH2:18][C@H:19]2[CH2:21][C@@H:20]2[CH3:22])[C:14]=1[C:23]([O:25][CH3:26])=[O:24])=[O:9]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 69367093methyl 4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate

Product 1

HCID 12110455Methyl 3-formyl-4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylateYield 78.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Phosphorus oxychloride (2.15 g, 14 mmol) was added to a solution of dimethylformamide (1.10 g, 15 mmol) in toluene (2 ml) and the mixture was stirred at room temperature for 30 minutes. To this mixture was added a solution of methyl 4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate (2.21 g, 10 mmol) in toluene (6 ml) and the mixture was heated at 80° C. for 10 hours. After the reaction was completed, the reaction mixture was poured into water and neutralized with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated in vacuo. The residue was chromatographed on a column using ethyl acetate/hexane=10/1 as the eluant to afford the title compound (1.95 g, 78.2%) as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated at 80° C. for 10 hours
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a column

Sources & evidence

ORD record
ord-bb5e9579c600449f872747af3e6c52b1
Source dataset
uspto-grants-2004_05
Patent number
US06734181B2

Reaction notes

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