Hydroxyamine chloride → methyl (E)-2-[2-[[4-[(E)-C-ethyl-N-hydroxycarbonimidoyl]-2,5-dimethylphenoxy]methyl]phenyl]-3-methoxyprop-2-enoate

HRID 1619160Notes

Reaction equation

HRID 1619160 reaction equation
[CH3:1][C:2]1[CH:23]=[C:22]([C:24](=O)[CH2:25][CH3:26])[C:21]([CH3:28])=[CH:20][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1/[C:12](=[CH:17]\[O:18][CH3:19])/[C:13]([O:15][CH3:16])=[O:14].[Cl-].[NH2:30][OH:31]>CO>[OH:31]/[N:30]=[C:24](/[C:22]1[C:21]([CH3:28])=[CH:20][C:3]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2/[C:12](=[CH:17]\[O:18][CH3:19])/[C:13]([O:15][CH3:16])=[O:14])=[C:2]([CH3:1])[CH:23]=1)\[CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 21878317Hydroxyamine chlorideHCID 67955272(E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate

Product 1

HCID 88531482methyl (E)-2-[2-[[4-[(E)-C-ethyl-N-hydroxycarbonimidoyl]-2,5-dimethylphenoxy]methyl]phenyl]-3-methoxyprop-2-enoateYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.17 g (0.44 mmol) of (E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate obtained in Step 3 and 0.06 g (0.88 mmol) of hydroxylamine chloride in 10 mL of methanol was added 0.8 g of a molecular sieve for dehydration. The reaction mixture was stirred at room temperature for 3 hours and filtered through celite and the filtrate was concentrated in a vacuum. The concentrate was stirred in water (10 mL) and extracted twice with 10 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified through silica gel chromatography to produce (E)-methyl 2-(2-((4-((E)-1-(hydroxyimino)propyl)-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate as a white solid (0.11 g, yield: 67%).

Workup

  1. filtrationfiltered through celite
  2. concentrationthe filtrate was concentrated in a vacuum
  3. stirringThe concentrate was stirred in water (10 mL)
  4. extractionextracted twice with 10 mL of dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationfollowed by vacuum concentration
  7. customThe residue was purified through silica gel chromatography

Sources & evidence

ORD record
ord-5cfcd446b09d4d2ba82fbe30b9248f18
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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