N-Hydroxyphthalimide → N-(3-(5-trifluoromethyl-2-pyridyloxy)propyl-oxy)phthalimide

HRID 1280251Notes

Reaction equation

HRID 1280251 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1.O[N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[F:14][C:12]([F:15])([F:13])[C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][O:1][N:17]2[C:18](=[O:27])[C:19]3=[CH:26][CH:25]=[CH:24][CH:23]=[C:20]3[C:21]2=[O:22])=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 112067993-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}propan-1-ol

Product 1

HCID 18430148N-(3-(5-trifluoromethyl-2-pyridyloxy)propyl-oxy)phthalimideYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 20.0 g of 2-(3-hydroxypropyloxy)-5-trifluoromethylpyridine, 14.7 g of N-hydroxyphthalimide, 23.6 g of triphenylphosphine, and 200 ml of tetrahydrofuran was slowly added dropwise 20.0 g of diisopropyl azodicarboxylate with stirring under ice cooling in a stream of nitrogen gas. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to give a residue. This residue was subjected to silica gel chromatography, which afforded 27.8 g (yield, 84%) of N-(3-(5-trifluoromethyl-2-pyridyloxy)propyloxy)phthalimide, m.p., 97.6° C.

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. concentrationthe reaction mixture was concentrated
  3. customto give a residue

Sources & evidence

ORD record
ord-880ddbf71a2e47f98befac1d845b9a5e
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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