Triethylamine → 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-2-methylpropanal

HRID 1892042Notes

Reaction equation

HRID 1892042 reaction equation
[OH:1][CH2:2][C:3]([N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16])([CH3:5])[CH3:4].C(N(CC)CC)C>CS(C)=O>[O:16]=[C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14](=[O:15])[N:6]1[C:3]([CH3:5])([CH3:4])[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 8277892-(1-hydroxy-2-methylpropan-2-yl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 145786772-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-2-methylpropanalYield 90.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

11.9 g of sulfur trioxide pyridine complex dissolved in 75 ml DMSO was added over a period of 20 minutes at room temperature to a solution of 5.48 g of 2-(2-hydroxy-1,1-dimethyl-ethyl)-isoindole-1,3-dione from Step 1 and 7.59 g of triethylamine in 780 ml DMSO. The reaction mixture was stirred at room temperature for 30 minutes, poured onto ice/water and extracted 3 times with tert-butyl methyl ether. The organic was washed with 1N HCl and 2 times H2O, dried over magnesium sulfate and the solvent was evaporated under reduced pressure to give 4.92 g crystals (mp 80-82° C.), which were used in the next step without further purification.

Workup

  1. additionpoured onto ice/water
  2. extractionextracted 3 times with tert-butyl methyl ether
  3. washThe organic was washed with 1N HCl and 2 times H2O
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a1080f6fd1964612b607db3a6bf5ca16
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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