Benzofuran-2,3-dione2-{o-[2-(tetrahydropyran-2-yloxy)-ethyl]-oxime} → Benzofuran-2,3-dione2-[o-(2-hydroxy-ethyl)-oxime]

HRID 1581820Notes

Reaction equation

HRID 1581820 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][O:10][N:11]=[C:12]1[C:16](=[O:17])[C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[O:13]1>CO>[OH:7][CH2:8][CH2:9][O:10][N:11]=[C:12]1[C:16](=[O:17])[C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[O:13]1

Participants

3

Reactant 1

HCID 54456798Benzofuran-2,3-dione2-{o-[2-(tetrahydropyran-2-yloxy)-ethyl]-oxime}

Product 1

HCID 54464037Benzofuran-2,3-dione2-[o-(2-hydroxy-ethyl)-oxime]Yield 81.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2.07 g (0.01 mol) of benzofuran-2,3-dione 2-{O-[2-(tetrahydropyran-2-yloxy)-ethyl]-oxime} (XIV-2) are dissolved in 12 ml of methanol and stirred at room temperature with 100 mg of acidic ion exchanger resin for 16 hours. 40 ml of methanol are added to the reaction mixture which is then warmed until the crystals have dissolved. The acidic ion exchanger resin is filtered off, the filtrate is concentrated and the residue is recrystallized from 10 ml of toluene. 1.69 g (81.5% of theory) of crystalline benzofuran-2,3-dione 2-[O-(2-hydroxy-ethyl)-oxime] (VII-1) of melting point 110-111° C. are obtained.

Workup

  1. temperatureis then warmed until the crystals
  2. dissolutionhave dissolved
  3. filtrationThe acidic ion exchanger resin is filtered off
  4. concentrationthe filtrate is concentrated
  5. customthe residue is recrystallized from 10 ml of toluene

Sources & evidence

ORD record
ord-76accefd5f8d41b09285d7ea1f1998a8
Source dataset
uspto-grants-2004_05
Patent number
US06730799B2

Reaction notes

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