Water → HCID 12015903, compound

HRID 989260Notes

Reaction equation

HRID 989260 reaction equation
C(O[CH:5]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:6]1)(=O)C.C[Si]([N:23]=[N+:24]=[N-:25])(C)C.Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.O>ClCCCl>[N:23]([CH:5]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:6]1)=[N+:24]=[N-:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24840Magnesium perchlorateHCID 78378AzidotrimethylsilaneHCID 12015902HCID 12015902, compound

Product 1

HCID 12015903HCID 12015903, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of the compound obtained in Step C (3.52 g/14.65 mmol) in 50 ml of 1,2-dichloroethane there are added dropwise trimethylsilyl azide (TMSN3), and then 0.326 g (1.46 mmol) of magnesium perchlorate (Mg(ClO4)2), and the whole is stirred at room temperature overnight. Hydrolysis is then carried out using H2O, followed by extraction with AcOEt; the organic phases are then combined, washed with a saturated NaCl solution, dried over MgSO4 and concentrated to dryness. The yellow oil so obtained is chromatographed over a column of silica gel (cyclohexane, 2% AcOEt) to yield the title product in the form of a translucent oil.

Workup

  1. customHydrolysis
  2. extractionfollowed by extraction with AcOEt
  3. washwashed with a saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe yellow oil so obtained
  7. customis chromatographed over a column of silica gel (cyclohexane, 2% AcOEt)

Sources & evidence

ORD record
ord-89cb1e43fb5640e293885fff355101e3
Source dataset
uspto-grants-2003_10
Patent number
US06638962B2

Reaction notes

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