Triphenylphosphine → (R)-2-[2-(2,5-difluorophenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione

HRID 478990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 478990
[OH:1][CH2:2][C@H:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1O.CCOC(/N=N/C(OCC)=O)=O>>[F:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1[O:1][CH2:2][C@H:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4]

Komponenten

5

Edukt 4

HCID 11776TriphenylphosphineHCID 949522,5-DifluorophenolHCID 6418462-[(2R)-1-hydroxypropan-2-yl]-2,3-dihydro-1H-isoindole-1,3-dioneHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 69472648(R)-2-[2-(2,5-difluorophenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dioneAusbeute 63,9 %

Versuchsvorschrift

A solution of 15.8 g (77 mmol) of (R)-2-(2-hydroxy-1-methylethyl)-1H-isoindole-1,3(2H)-dione, 24.2 g (92 mmol) of triphenylphosphine and 10.0 g (77 mmol) of 2,5-difluorophenol was stirred while 18.2 mL (116 mmol) of diethylazodicarboxylate was added dropwise. After stirring at ambient temperature overnight, solvent was removed and the residue was dissolved in ethyl acetate. The ethyl acetate was washed with water and brine. Drying (MgSO4) and removal of solvent gave an oil which was chromatographed on silica gel to give 15.6 g of the title compound of Step C as an oil, 1H NMR (CDCl3) δ1.55 (d, 3H), 4.25 (m, 1H), 4.8 (m, 1H), 6.55 (m, 1H), 6.65 (m, 1H), 6.9 (m, 1H), 7.7 (m, 2H), 7.85 (m, 2H).

Aufarbeitung

  1. additionwas added dropwise
  2. customsolvent was removed
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe ethyl acetate was washed with water and brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent
  7. customgave an oil which
  8. customwas chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1ac482ab46d841138e47e1af4e3fa5dc
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642392B1

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