Dichloromethane → Ethyl 5-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-2-formyl-1H-pyrrol-3-carboxylate

HRID 2097532Notes

Reaction equation

HRID 2097532 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:16]3[NH:20][C:19]([CH2:21][O:22]CC4C=CC(OC)=CC=4)=[C:18]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:17]=3)[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:3][CH2:2]1.ClCCl.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:16]3[NH:20][C:19]([CH:21]=[O:22])=[C:18]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:17]=3)[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 66602560Ethyl 5-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-2-(4-methoxybenzyloxymethyl)-1H-pyrrol-3-carboxylate

Product 1

HCID 86627053Ethyl 5-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-2-formyl-1H-pyrrol-3-carboxylateYield 50.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10.3 g (20.6 mmol) of ethyl 5-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-2-(4-methoxybenzyloxymethyl)-1H-pyrrol-3-carboxylate obtained in Reference example 45-(c) were added 100 ml of dichloromethane and 10 ml of water, then, 5.15 g (22.7 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was added to the mixture under ice-cooling, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction suspension was filtered through Celite, the filtrate was successively washed with a saturated aqueous solution of sodium hydrogencarbonate, and then, with a saturated aqueous solution of sodium chloride. The organic layer after separation was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. To the obtained concentrate was added 100 ml of a mixed solvent (diisopropyl ether/hexane=1/1 (V/V)), and the precipitated solid was collected by filtration. The obtained solid was washed with diisopropyl ether, and dried under reduced pressure to obtain 3.98 g of the title compound as a pale yellowish solid. (Yield: 49%)

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. filtrationthe reaction suspension was filtered through Celite
  4. washthe filtrate was successively washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. customThe organic layer after separation
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. concentrationTo the obtained concentrate
  9. additionwas added 100 ml of a mixed solvent (diisopropyl ether/hexane=1/1 (V/V))
  10. filtrationthe precipitated solid was collected by filtration
  11. washThe obtained solid was washed with diisopropyl ether
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-ef6c123d728e426ea02ee60b91d4a022
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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