Water → [3-(2-Fluoroethoxymethyl)-5-methoxyphenyl]methanol

HRID 1698720Notes

Reaction equation

HRID 1698720 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[C:7]([CH2:9][OH:10])[CH:8]=1.[H-].[Na+].[F:15][CH2:16][CH2:17]I.O>CN(C=O)C.C(OCC)(=O)C>[F:15][CH2:16][CH2:17][O:12][CH2:11][C:5]1[CH:6]=[C:7]([CH2:9][OH:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69804Ethane, 1-fluoro-2-iodo-HCID 4114928(3-(Hydroxymethyl)-5-methoxyphenyl)methanol

Product 1

HCID 59517408[3-(2-Fluoroethoxymethyl)-5-methoxyphenyl]methanolYield 11.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1 g of 5-methoxy-1,3-benzenedimethanol in 10 ml of DMF there was added 238 mg of sodium hydride (60% oily suspension) at 0° C. After stirring at room temperature for 30 minutes, 1.04 g of 1-fluoro-2-iodoethane was added and the mixture was stirred at room temperature for 22 hours. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (145 mg) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 22 hours
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-afad464da59c498b8cd91fbd8012775a
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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