Diethyl Ether → HCID 68697439, compound

HRID 1951761Notes

Reaction equation

HRID 1951761 reaction equation
I[CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.CCOCC.[Mg].[CH3:14][N:15]([CH3:28])[C:16]1(C#N)[CH2:25][CH2:24][C:19]2([O:23][CH2:22][CH2:21][O:20]2)[CH2:18][CH2:17]1>C1COCC1>[CH:3]1([CH2:2][C:16]2([N:15]([CH3:28])[CH3:14])[CH2:25][CH2:24][C:19]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:18][CH2:17]2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 3283Diethyl Ether3×HCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 2762531(Iodomethyl)cyclopentaneHCID 5462224Magnesium

Product 1

HCID 68697439HCID 68697439, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of iodomethylcyclopentane (31.5 g, 150 mmol) in abs. ether (150 ml) was added dropwise to a mixture of magnesium (3.64 g, 150 mmol) in abs. ether (30 ml) in such a manner that the ether boiled slightly. Then the reaction solution was boiled under reflux for 30 min. and cooled to RT, and a solution of 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile B-1 (10.5 g, 50 mmol) in abs. THF (100 ml) was added dropwise. The reaction solution began to boil and a white solid precipitated. Boiling was carried out for 6 h under reflux, followed by stirring overnight at RT. For working up of the reaction mixture, 20% NH4Cl solution (200 ml) was added, while cooling with ice, and extraction with ether (3×100 ml) was carried out. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue that remained was purified by flash chromatography with EA/EtOH (20:1).

Workup

  1. temperatureunder reflux for 30 min.
  2. customa white solid precipitated
  3. temperatureunder reflux
  4. additionwas added
  5. temperaturewhile cooling with ice, and extraction with ether (3×100 ml)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue that remained was purified by flash chromatography with EA/EtOH (20:1)

Sources & evidence

ORD record
ord-25b87c22664c46aa867b4c66b3be8063
Source dataset
uspto-grants-2013_03
Patent number
US08404740B2

Reaction notes

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