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

HRID 726713

반응식

HRID 726713 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매4회

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-882f43c3752d4cfaa7db48613ec305ff
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05710159

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