Sodium Carbonate → Diethyl 4-((hydroxyimino)(4-methoxyphenyl)methyl)benzylphosphonate

HRID 1525313Notes

Reaction equation

HRID 1525313 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([C:7]([C:9]2[CH:23]=[CH:22][C:12]([CH2:13][P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)=O)=[CH:5][CH:4]=1.Cl.[NH2:27][OH:28].C([O-])([O-])=O.[Na+].[Na+]>CCO>[OH:28][N:27]=[C:7]([C:6]1[CH:24]=[CH:25][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:9]1[CH:23]=[CH:22][C:12]([CH2:13][P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 89462655Diethyl 4-(4-methoxybenzoyl)benzylphosphonate

Product 1

HCID 131733145Diethyl 4-((hydroxyimino)(4-methoxyphenyl)methyl)benzylphosphonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl 4-(4-methoxybenzoyl)benzylphosphonate, 32-d, (500 mg, 1.38 mmol) was dissolved in 95% EtOH (5 ml). Hydroxylamine hydrochloride (288 mg, 4.14 mmol) and Na2CO3 (439 mg, 4.14 mmol) was added to the solution. The reaction mixture was then stirred for 10 h under reflux. The resulting mixture was cooled to ambient temperature, filtered. The filtrate was concentrated under reduce pressure, extracted with ethyl acetate/H2O (3×10 ml). The organic layer was combined and washed with brine (2×10 ml) dried over Na2SO4 anhydrous, concentrated under reduce pressure to dry. The pure product, 32-e, was obtained as colorless oil (460 mg, 88% yield). 1H NMR (300 MHz, CDCl3) δ 0.67-0.85 (m, 6H), 2.628-3.306 (m, 2H), 3.30-3.35 (d, J=46.8, 3H), 3.51-3.63 (m, 4H), 6.31-6.33 (m, 1H), 6.44-6.47 (m, 1H), 6.74-6.92 (m, 6H). LC-MS 378 [MH]+.

Workup

  1. temperatureunder reflux
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. extractionextracted with ethyl acetate/H2O (3×10 ml)
  5. washwashed with brine (2×10 ml)
  6. dry with materialdried over Na2SO4 anhydrous
  7. concentrationconcentrated
  8. customto dry

Sources & evidence

ORD record
ord-2f050af58b0a4e948d98c12827e0ef04
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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