Methyl iodide → 8-Methoxy-8-(trifluoromethyl)-1,4-dioxaspiro[4.5]decane

HRID 922118Notes

Reaction equation

HRID 922118 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1([OH:13])[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1.[H-].[Na+].I[CH3:19]>O1CCCC1>[CH3:19][O:13][C:3]1([C:2]([F:1])([F:14])[F:15])[CH2:4][CH2:5][C:6]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 616452568-(Trifluoromethyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 712468178-Methoxy-8-(trifluoromethyl)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., 16.23 g (71.75 mmol) of 8-(trifluoromethyl)-1,4-dioxaspiro[4.5]decan-8-ol (Example 7A) were dissolved in 582 ml of tetrahydrofuran, 5.74 g (143.50 mmol) of sodium hydride (60% in paraffin oil) were added a little at a time and the mixture was stirred at room temperature for 1 hour. 50.92 g (358.76 mmol) of iodomethane were added dropwise to the resulting suspension, and the reaction mixture was stirred at room temperature overnight. For work-up, the mixture was poured into about 1 l of ice-water and the product was extracted with dichloromethane. The organic phase was washed repeatedly with water, dried over sodium sulphate and concentrated under reduced pressure. Drying gave 17.34 g (100% of theory) of the title compound as a brownish oil.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionthe product was extracted with dichloromethane
  3. washThe organic phase was washed repeatedly with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customDrying

Sources & evidence

ORD record
ord-95199e1828cd4fafbdd528bb80aaa5c2
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

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