Water → 1H-Pyrrole-3-carboxaldehyde, 1-(phenylsulfonyl)-

HRID 2121357Notes

Reaction equation

HRID 2121357 reaction equation
C[O:2][CH:3]1[CH:7]([CH:8]=O)[CH2:6][CH:5](OC)O1.[C:12]1([S:18]([NH2:21])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:12]1([S:18]([N:21]2[CH:5]=[CH:6][C:7]([CH:3]=[O:2])=[CH:8]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 7370BenzenesulfonamideHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde

Product 1

HCID 110643801H-Pyrrole-3-carboxaldehyde, 1-(phenylsulfonyl)-Yield 88.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5.91 g (0.037 mol) of 2,5-dimethoxytetrahydrofuran-3-carbaldehyde, 5.80 g (0.037 mol) of phenylsulfonamide and a spatula tip of 4-toluenesulfonic acid in 50 ml of toluene was refluxed with a water trap until water no longer separated out. The reaction mixture was washed three times with water. The organic phase was dried over magnesium sulfate with addition of activated carbon and silica gel and concentrated in vacuo. 7.68 g of a brown resin were obtained.

Workup

  1. customno longer separated out
  2. washThe reaction mixture was washed three times with water
  3. dry with materialThe organic phase was dried over magnesium sulfate with addition of activated carbon and silica gel
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9ec9869b6064ce7bb68f1685037d712
Source dataset
uspto-grants-2004_02
Patent number
US06696437B1

Reaction notes

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