N-Hydroxyphthalimide → N-(3-methylisoxazol-5-yl)methoxyphthalimide

HRID 1451557Notes

Reaction equation

HRID 1451557 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:33][C:34]1[O:38][N:37]=[C:36]([CH3:39])[CH:35]=1.N(C(OC)=O)=NC(OC)=O>O1CCCC1>[CH3:39][C:36]1[CH:35]=[C:34]([CH2:33][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])[O:38][N:37]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl esterHCID 10820493(3-Methylisoxazol-5-yl)methanol

Product 1

HCID 19974982N-(3-methylisoxazol-5-yl)methoxyphthalimideYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8.17 g of N-hydroxyphthalimide and 23.9 g of triphenylphosphine were added to a solution of 5.15 g of 5-hydroxymethyl-3-methylisoxazole in 245 ml of tetrahydrofuran. A solution of 13.3 g of dimethyl azodicarboxylate in 20 ml of tetrahydrofuran was then added dropwise at room temperature under an atmosphere of nitrogen to the resulting solution. The mixture was then allowed to stand for 30 minutes, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by flash column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to afford 7.21 g of N-(3-methylisoxazol-5-yl)methoxyphthalimide, melting at 129°-131° C.

Workup

  1. customafter which the solvent was removed by distillation under reduced pressure
  2. customThe resulting residue was purified by flash column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-d81cf70d3cc24cc99ab2dd50d3e5788c
Source dataset
uspto-grants-1997_02
Patent number
US05604256

Reaction notes

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