Triethylamine → N-hydroxy-2,2-dimethylspiro[1,3-dioxane-5,2'-inden]-1'(3'H)-imine

HRID 64451Notes

Reaction equation

HRID 64451 reaction equation
[CH3:1][C:2]1([CH3:17])[O:16][CH2:15][C:5]2([CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=O)[CH2:4][O:3]1.Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+].C(N(CC)CC)C>C(O)C.C(OCC)(=O)C.O>[OH:20][N:19]=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][C:5]21[CH2:15][O:16][C:2]([CH3:17])([CH3:1])[O:3][CH2:4]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 71108842HCID 71108842, compound

Product 1

HCID 86713466N-hydroxy-2,2-dimethylspiro[1,3-dioxane-5,2'-inden]-1'(3'H)-imineYield 93.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1 g of 2,2-dimethylspiro[1,3-dioxane-5,2′-inden]-1′(3′H)-one, 329 mg of hydroxylamine hydrochloride, and 388 mg of sodium acetate in 5 ml of ethanol was stirred for 12 hours. Then, 1.2 ml of triethylamine was added thereto, followed by stirring at room temperature for 3 days and further stirring at 50° C. for 1 hour. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.0 g of N-hydroxy-2,2-dimethylspiro[1,3-dioxane-5,2′-inden]-1′(3′H)-imine.

Workup

  1. stirringby stirring at room temperature for 3 days
  2. stirringfurther stirring at 50° C. for 1 hour
  3. customa layer separation operation
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bd9a5799797542bea9c5897d9a74b661
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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