Triphenylphosphine → 2-[3-(2-Oxo-2H-1-benzopyran-4-yloxy)-propyl]-isoindole-1,3-dione

HRID 495153Notes

Reaction equation

HRID 495153 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[CH2:33][CH2:34][CH2:35][N:36]1[C:44](=[O:45])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]1=[O:46].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[O:12]=[C:4]1[CH:3]=[C:2]([O:1][CH2:33][CH2:34][CH2:35][N:36]2[C:44](=[O:45])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]2=[O:46])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:5]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 701602-(3-Hydroxypropyl)isoindoline-1,3-dioneHCID 5363146Diisopropyl azodicarboxylateHCID 546829304-Hydroxycoumarin

Product 1

HCID 113939422-[3-(2-Oxo-2H-1-benzopyran-4-yloxy)-propyl]-isoindole-1,3-dioneYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-hydroxycoumarin (6.17 mmol, 1.0 g), PPh3 (6.48 mmol, 1.70 g), and 2-(3-hydroxy-propyl)-isoindole-1,3-dione (6.48 mmol, 1.33 g) is disolved in 20 mL THF and is cooled to 0° C. DIAD (6.79 mmol, 1.33 mL) is added dropwise at 0° C. A precipitate is formed immediately and the reaction mixture thickens. The precipitate is filtered, is washed with Et2O and is dried to afford the title compound (1.62 g, 75%). 1H NMR (DMSO-d6, 300 MHz) δ 7.82 (4H, m), 7.61 (2H, m), 7.37 (1H, m), 7.21 (1H, m), 5.83 (1H, s), 4.28 (2H, t, J=5.75 Hz), 3.83 (2H, t, J=6.25 Hz), 2.19 (2H, m); MS (ESI, Pos.) calcd for C20H15NO5 m/z [M+H]=350.1, found 350.1.

Workup

  1. customA precipitate is formed immediately
  2. filtrationThe precipitate is filtered
  3. washis washed with Et2O
  4. customis dried

Sources & evidence

ORD record
ord-c50f7bb7b5334a26a7469c9b87a28d4b
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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