Water → 2-[2-(3-Dimethoxymethyl-2-fluoro-5-methoxybenzyloxy]ethoxy]tetrahydropyran

HRID 1161579Notes

Reaction equation

HRID 1161579 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4]1[C:5]([F:14])=[C:6]([CH2:12][OH:13])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1.[H-].[Na+].Br[CH2:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1.O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:16][O:15][CH:3]([O:2][CH3:1])[C:4]1[C:5]([F:14])=[C:6]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:12][O:13][CH2:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 59517072(3-Dimethoxymethyl-2-fluoro-5-methoxyphenyl)methanol

Product 1

HCID 595174642-[2-(3-Dimethoxymethyl-2-fluoro-5-methoxybenzyloxy]ethoxy]tetrahydropyran

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

(3-Dimethoxymethyl-2-fluoro-5-methoxyphenyl)methanol (1.861 g) was dissolved in 10 ml of DMF, and 390 mg of sodium hydride, 300 mg of tetrabutylammonium iodide, and 1.8 ml of 2-(2-bromoethoxy)tetrahydropyran were added thereto. The mixture was stirred at room temperature for 2 hours, and then water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate) to give the title compound (1.035 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe desiccating agent was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate)

Sources & evidence

ORD record
ord-90834be7c332453b843867acf42dd64d
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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