Tetrahydrofuran → HCID 18177295, compound

HRID 2186207Notes

Reaction equation

HRID 2186207 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH:7]=[N:8][OH:9])=[CH:5][CH:4]=1.C[O:13][C:14](=[O:21])[C:15]([CH2:17][C:18]([OH:20])=[O:19])=[CH2:16].[CH2:22]1COCC1>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[CH2:16][C:15]([C:14]([OH:13])=[O:21])([CH2:17][C:18]([O:20][CH3:22])=[O:19])[O:9][N:8]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 94712N-[(4-Methoxyphenyl)methylidene]hydroxylamineHCID 4613903Butanedioic acid, 2-methylene-, methyl ester

Product 1

HCID 18177295HCID 18177295, compoundYield 58%

Procedure

4-Methoxybenzaldehyde oxime (5.00 g, 33.1 mmol) and itaconic acid monomethyl ester (5.72 g, 39.7 mol) were added together with 200 mL of THF. To the above mixture was added bleach (84 mL of 0.67M aqueous solution) dropwise at room temperature. The reaction mixture was then stirred at RT under N2 for 12 h. The THF was removed in vacuo. The aqueous mixture was acidified with aqueous HCl and extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, concentrated, and chromatographed with 10-30% MeOH in CH2Cl2 on silica gel to give 5.58 g of the desired product (58%). 1H NMR (DMSO-d6): δ3.08 (m, 2H); 3.61 (s, 3H); 3.55-3.87 (m, 2H); 3.80 (s, 3H);7.00 (d, 2H); 7.61 (d, 2H).

Workup

  1. customThe THF was removed in vacuo
  2. extractionextracted with EtOAc
  3. washThe EtOAc solution was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed with 10-30% MeOH in CH2Cl2 on silica gel

Sources & evidence

ORD record
ord-9506826b9a764f79bd65ae3e278dbf27
Source dataset
uspto-grants-2002_06
Patent number
US06403620B1

Reaction notes

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