Water → Benzyl 5-formyl-1H-pyrrole-2-carboxylate

HRID 1469662Notes

Reaction equation

HRID 1469662 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[NH:12][CH:13]=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([CH:19]=[O:20])C.P(Cl)(Cl)(Cl)=O.O>ClCCCl>[CH2:1]([O:8][C:9]([C:11]1[NH:12][C:13]([CH:19]=[O:20])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 8543774HCID 8543774, compound

Product 1

HCID 71349636Benzyl 5-formyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Next, To a stirred solution of 1H-pyrrole-2-carboxylic acid benzylester (2.0 g, 9.94 mmol) in 1,2-dichloroethane (15 mL) at 5° C. is sequentially added DMF (1.12 g, 15.31 mmol) and phosphoryl trichloride (2.35 g, 15.31 mmol). After the addition, the mixture is heated to 50° C. and stirred for an hour. Water is added and the mixture is extracted with ethyl acetate (3×). The combined organic layers are washed with water and brine then is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (heptane/ethyl acetate=3:1) to give 5-formyl-1H-pyrrole-2-carboxylic acid benzyl ester; HPLC Retention time 1.64 minutes (condition C): MS 230.3 (M+1).

Workup

  1. customat 5° C.
  2. additionAfter the addition
  3. extractionthe mixture is extracted with ethyl acetate (3×)
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialthen is dried over magnesium sulfate
  6. customThe solvent is removed under reduced pressure
  7. customthe residue is purified by flash chromatography (heptane/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-3c47056869224322a67aab7a79ed790f
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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