Water → 4-(5-fluoro-2-nitrophenoxy)tetrahydro-2H-pyran

HRID 1042121Notes

Reaction equation

HRID 1042121 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.CS(O[CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:7]=1)[O:8][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

8

Reactant 4

HCID 962WaterHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium CarbonateHCID 11344352Oxan-4-yl methanesulfonate

Product 1

HCID 533521804-(5-fluoro-2-nitrophenoxy)tetrahydro-2H-pyranYield 90%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-fluoro-2-nitrophenol (100 g), tetrahydro-2H-pyran-4-yl methanesulfonate (172 g) and potassium carbonate (176 g) in N,N-dimethylformamide (1000 mL) was stirred at 50° C. for 3 days. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=0:100 to 25:75, volume ratio) to give the title compound (138 g, yield 90%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crude product

Sources & evidence

ORD record
ord-ec5985c978f64901878b44708184b7f1
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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