Diethyl Ether → HCID 86626342, compound

HRID 907606Notes

Reaction equation

HRID 907606 reaction equation
[F:1][C:2]([F:17])([O:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[C:3]([N:5]([O:7][CH3:8])[CH3:6])=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].C(OCC)C>C1COCC1>[F:17][C:2]([F:1])([O:9][C:10]1[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=1)[CH:3]([N:5]([O:7][CH3:8])[CH3:6])[OH:4]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86626341HCID 86626341, compound

Product 1

HCID 86626342HCID 86626342, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,2-difluoro-2-(4-fluorophenoxy)-N-methoxy-N-methylacetamide (2.03 g, 8.1 mmol) in anhydrous THF (15 ml) at 0° C., a solution of 1 M of lithium aluminum hydride in THF (4.05 ml, 4.05 mmol) was added. After stirring the solution for 3 h, 1N NaOH (2 ml) and ethyl ether (15 ml) were added. After 30 min, the reaction mixture was filtered through Celite and the cake was washed several times with ethyl ether. The organic phase was washed with brine and dried over sodium sulfate. The solvent was removed and the crude was purified using a short plug of silica gel to give 2,2-difluoro-2-(4-fluorophenoxy)-1-(N-methoxy-N-methylamino)ethanol as an oil (1.15 g, 57%).

Workup

  1. waitAfter 30 min
  2. filtrationthe reaction mixture was filtered through Celite
  3. washthe cake was washed several times with ethyl ether
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed
  7. customthe crude was purified

Sources & evidence

ORD record
ord-f4c717a4e68542428b63f88100eca090
Source dataset
uspto-grants-2011_09
Patent number
US08013186B2

Reaction notes

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