Triphenylphosphine → 2-[5-Chloro-2-(3-methylisoxazol-5-ylmethoxy)benzyl]isoindole-1,3-dione

HRID 392919

Reaction equation

HRID 392919 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([CH:19]=1)[CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].O[CH2:22][C:23]1[O:27][N:26]=[C:25]([CH3:28])[CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:22][C:23]2[O:27][N:26]=[C:25]([CH3:28])[CH:24]=2)=[C:6]([CH:19]=1)[CH2:7][N:8]1[C:9](=[O:18])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]1=[O:17]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10820493(3-Methylisoxazol-5-yl)methanolHCID 219732982-[5-Chloro-2-hydroxy benzyl]isoindole-1,3-dione

Product 1

HCID 226617672-[5-Chloro-2-(3-methylisoxazol-5-ylmethoxy)benzyl]isoindole-1,3-dioneYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-[5-chloro-2-hydroxy benzyl]isoindole-1,3-dione (800 mg, 2.78 mmol), 5-hydroxymethyl-3-methyl-isoxazole (373 mg, 3.3 mmol), and triphenylphosphine (1.0 g, 4.2 mmol) in anhydrous THF (10 mL) was added diethylazodicarboxylate (0.657 mL, 4.7 mmol). The solution was stirred for 15 h at room temperature under anhydrous conditions. The solvent was then removed by rotary evaporation and the product was preadsorbed onto silica gel and purified by flash chromatography to afford the title compound (555 mg, 52%).

Workup

  1. customThe solvent was then removed by rotary evaporation
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-3127d714a8fd4ac9837dc84b1d6b7271
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Linked notes

Loading…