Triphenylphosphine → HCID 22610095, compound

HRID 2306661Notes

Reaction equation

HRID 2306661 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12](=[N:14][OH:15])[CH3:13])[C:5]([O:7][CH3:8])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:13][C:12]1[C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[O:15][N:14]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 136347709HCID 136347709, compound

Product 1

HCID 22610095HCID 22610095, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 3-hydroxy-4-[N-hydroxyethanimidoyl]benzoate (250 mg, 1.19 mmole) is combined with triphenylphosphine (446 mg, 1.7 mmole) in 14 ml dry THF in a dry flask under nitrogen. The solution is treated slowly dropwise with N,N′-diethylazidodicarboxylate (268 mL, 1.7 mmole) in 10 ml dry THF. The reaction is stirred 4 h at rt. The volatiles are removed in vacuo and the residue is chromatographed over 30 g silica gel (230-400 mesh) eluting with 10% EtOAc/hexane. The appropriate fractions are combined and concentrated to provide 125 mg (55%) of methyl 3-methyl-1,2-benzisoxazole-6-carboxylate slightly contaminated (<10%) with methyl 4-acetyl-3-hydroxybenzoate. 1H NMR (CDCl3) δ 2.64, 4.00, 7.70, 8.01, 8.25 ppm.

Workup

  1. customThe volatiles are removed in vacuo
  2. customthe residue is chromatographed over 30 g silica gel (230-400 mesh)
  3. washeluting with 10% EtOAc/hexane
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e0f09909c7a7426495b783202ae07d05
Source dataset
uspto-grants-2004_12
Patent number
US06828330B2

Reaction notes

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