Dimethyl Sulfoxide → 1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal

HRID 726713

Reaction equation

HRID 726713 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C(N(CC)CC)C>ClCCl>[O:11]=[CH:12][CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 111175282-(4-hydroxybutyl)-1H-Isoindole-1,3(2H)-dione

Product 1

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-78 °C

Procedure

Oxalyl Chloride (4.01 ml; 46 mmol) in 90 ml dichloromethane was cooled at -78° C. in a dry ice-acetone bath. Dimethylsulfoxide (4.26 ml; 60 mmol) in 22 ml dichloromethane was then added dropwise and the mixture stirred at -78° C. for 30 minutes. N-(4-Hydroxybutyl)phthalimide (9.108 g; 41.5 mmol) in 45 ml dichloromethane was then added and the mixture stirred in the -78° C. bath for 45 minutes. The mixture was then warmed in a 0° C. ice bath and stirred for one hour. Triethylamine (23 g; 230 mmol) in 23 ml dichloromethane was then added and the stirred for an additional 30 minutes. The mixture was worked up by washing with water. The organic layer was separated, dried (MgSO4), filtered, concentrated and the residue purified by flash chromatography; 200 g silica gel column using 1:3 ethyl acetate:Hexane to provide N-(4-oxobutyl)phthalimide as a white solid (7.469 g; 82.8% yield). 1 H NMR (300 MHz, CDCl3): 2.023 (m, 2H); 2.546 (dt, 2H, J1 =7.324 Hz, J2 =1.098 Hz); 3.749 (t, 2H, J=6.958 Hz); 7.734 (m, 2H); 7.845 (m, 2H); 9.777 (t, 1H, J=1.099 Hz).

Workup

  1. stirringthe mixture stirred in the -78° C. bath for 45 minutes
  2. temperatureThe mixture was then warmed in a 0° C. ice bath
  3. stirringstirred for one hour
  4. stirringthe stirred for an additional 30 minutes
  5. washby washing with water
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-882f43c3752d4cfaa7db48613ec305ff
Source dataset
uspto-grants-1998_01
Patent number
US05710159

Linked notes

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