Diethyl Ether → HCID 23331799, compound

HRID 224666Notes

Reaction equation

HRID 224666 reaction equation
[CH:1]([O-:6])([O-])[O:2][CH2:3][CH3:4].[C:7]([C:15]1[CH:19]=[C:18]([CH3:20])[N:17]([CH:21]([CH3:24])C=O)[C:16]=1[CH3:25])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:26][CH2:27]OCC>S(=O)(=O)(O)O>[CH2:26]([O:6][CH:1]([O:2][CH2:3][CH3:4])[CH:21]([N:17]1[C:18]([CH3:20])=[CH:19][C:15]([C:7](=[O:14])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:16]1[CH3:25])[CH3:24])[CH3:27]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 23331769HCID 23331769, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 23331799HCID 23331799, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Ethyl orthoformate (2 ml) and one drop of conc. sulfuric acid were added to 257 mg (1.0 mmole) of 2-(3-benzoyl-2,5-dimethylpyrrol-1-yl)propionaldehyde, and the reaction was performed at room temperature for 5 hours. Ether was added, and the organic layer was washed with water, dried, concentrated and chromatographed on a column of silica gel to afford compound (904) (82 mg, 0.25 mmole, 25%).

Workup

  1. washthe organic layer was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customchromatographed on a column of silica gel

Sources & evidence

ORD record
ord-a8c2f64b9b9247dda187dfb903df2317
Source dataset
uspto-grants-1980_11
Patent number
US04233309

Reaction notes

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