Water → HCID 68600580, compound

HRID 1951983Notes

Reaction equation

HRID 1951983 reaction equation
[H-].[Na+].[C:3]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([F:15])[CH:9]=1)(=[O:5])[CH3:4].[CH3:16][O:17][CH2:18][CH2:19][O:20][CH2:21]Cl.O>O1CCCC1.CN(C)C=O>[C:3]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:10]([F:15])[CH:9]=1)(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 68602191HCID 68602191, compound

Product 1

HCID 68600580HCID 68600580, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.6 g (65.1 mmol) of 60% sodium hydride is added in portions to a solution at 0° C. of 10 g (54.3 mmol) of (3-fluoro-4-hydroxy-phenyl)-methyl acetate diluted in 50 ml of tetrahydrofuran and 50 ml of dimethylformamide. The reaction mixture is stirred at room temperature for 45 minutes and then 6.8 ml (59.7 mmol) of 2-methoxyethoxymethyl chloride is added dropwise. The reaction mixture is stirred at room temperature for 2 hours and then the reaction mixture is treated by adding water and extracted with ethyl acetate. The organic phases are combined, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. The raw product is purified by silica column chromatography, eluted with a heptane/ethyl acetate mixture 70/30. 9.7 g (65%) of [3-fluoro-4-(2-methoxy-ethoxymethoxy)-phenyl]-methyl acetate is obtained in the form of a colorless oil.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 2 hours
  2. additionthe reaction mixture is treated
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe raw product is purified by silica column chromatography
  9. washeluted with a heptane/ethyl acetate mixture 70/30

Sources & evidence

ORD record
ord-cc451ea669a54e92a9a306d06b01380c
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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