Water → HCID 12390807, compound

HRID 1382362Notes

Reaction equation

HRID 1382362 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH3:14])=[C:12]([C:15](OC)=[O:16])[C:11]([C:19](OC)=[O:20])=[C:10]2[CH3:23])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].O>ClCCl.CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH3:14])=[C:12]([CH2:15][OH:16])[C:11]([CH2:19][OH:20])=[C:10]2[CH3:23])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 166653HydrideHCID 12390798HCID 12390798, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12390807HCID 12390807, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of dimethyl N-(4-methoxyphenyl)-2,5-dimethylpyrrole-3,4-dicarboxylate (0.04 mol) in dry dichloromethane (50 mL) was added dropwise over a 15-min period to a mechanically stirred mixture of lithium aluminum hydride (3.4 g, 0.08 mol) in anhydrous ether (100 mL) heated under reflux (50°-55° C. bath). The stirred mixture was heated under reflux for 1 h after the addition was complete and then cooled in an ice bath. The excess hydride was carefully decomposed with small additions of wet ether and then with water until the salts were white. The mixture was filtered (medium-porosity sintered-glass funnel) and the inorganic residue was washed with several portions of hot dichloromethane (about 30 mL) until the total filtrate volume was about 400 mL. The filtrate was concentrated in vacuo to a volume of about 125 mL, warmed to boiling, and diluted with slow portionwise addition of petroleum ether (about 100 mL) to yield 91% of N-(4-methoxyphenyl)-2,5-dimethyl-3,4-bis(hydroxymethyl)pyrrole: mp 143°-145° C. (dec).

Workup

  1. temperatureheated
  2. temperatureunder reflux (50°-55° C. bath)
  3. temperatureThe stirred mixture was heated
  4. temperatureunder reflux for 1 h
  5. additionafter the addition
  6. temperaturecooled in an ice bath
  7. filtrationThe mixture was filtered (medium-porosity sintered-glass funnel)
  8. washthe inorganic residue was washed with several portions of hot dichloromethane (about 30 mL) until the total filtrate volume
  9. concentrationThe filtrate was concentrated in vacuo to a volume of about 125 mL
  10. temperaturewarmed
  11. additiondiluted with slow portionwise addition of petroleum ether (about 100 mL)

Sources & evidence

ORD record
ord-f7b5deb96e534b60b531ed4c801842fc
Source dataset
uspto-grants-1989_02
Patent number
US04806561

Reaction notes

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