Trimethyl orthoformate → ethyl 4-formyl-5-methyl-1H-pyrrole-2-carboxylate

HRID 2233817Notes

Reaction equation

HRID 2233817 reaction equation
[CH3:1][O:2]C(OC)OC.[CH3:8][C:9]1[NH:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:10]=1>C(O)(C(F)(F)F)=O>[CH:1]([C:10]1[CH:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:13][C:9]=1[CH3:8])=[O:2]

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 965981H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl ester2×

Product 1

HCID 809639ethyl 4-formyl-5-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trimethoxymethane (1.18 ml, 10.78 mmol) was added to a solution of ethyl 5-methyl-1H-pyrrole-2-carboxylate (Intermediate 20) (0.5 g, 3.26 mmol) in TFA (2.5 ml) at 0° C. The reaction was stirred at that temperature for 10 mins then quenched with cold water (20 ml). The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried over magnesium sulfate and concentrated to give yellow solid which was purified by flash chromatography (10% to 20% EtOAc in hexanes, 0.25 g).

Workup

  1. customthen quenched with cold water (20 ml)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give yellow solid which
  7. customwas purified by flash chromatography (10% to 20% EtOAc in hexanes, 0.25 g)

Sources & evidence

ORD record
ord-739f64eee23e4930873e220009a83631
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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