Water → HCID 67957852, compound

HRID 1475627Notes

Reaction equation

HRID 1475627 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[C:12](=[O:13])[O:11][C:10]([CH3:15])([CH3:14])O[C:8]2=O)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].O.[CH2:23]1COCC1>C(O)(C)(C)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7](=[CH2:8])[C:12]([O:11][C:10]([CH3:23])([CH3:15])[CH3:14])=[O:13])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 67959550HCID 67959550, compound

Product 1

HCID 67957852HCID 67957852, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

11.1 g of 5-(4-chloro-3-nitrobenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (contaminated by residual 1,3-diisopropylurea) were dissolved in 40 ml of THF and 40 ml (31 g) of tert-butanol, and 16.4 g (88.5 mmol) of N,N-dimethylmethyleneiminium iodide were added. The resulting suspension was stirred at 70° C. overnight and then, after cooling, added to water. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10→50:1). This gave 8.22 g of the target product (about 78% of theory).

Workup

  1. temperatureafter cooling
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. washThe combined organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10→50:1)

Sources & evidence

ORD record
ord-cf84e63feec44f2ab18532de1b88ed56
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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