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Water → 2-[(Methylsulfonyl)methyl]-5-[4-nitro-3-(tetrahydro-2H-pyran-4-yloxy)phenoxy]pyridine

HRID 1042116
Notes
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Reaction equation

HRID 1042116 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([CH:14]=1)[O:7][CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[CH3:18][S:19]([CH2:22][C:23]1[N:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)(=[O:21])=[O:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[CH3:18][S:19]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][C:2]2[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([O:7][CH:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[CH:14]=2)=[CH:27][N:28]=1)(=[O:21])=[O:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 533521804-(5-fluoro-2-nitrophenoxy)tetrahydro-2H-pyranHCID 667261886-[(Methylsulfonyl)methyl]pyridin-3-ol

Product 1

HCID 667262242-[(Methylsulfonyl)methyl]-5-[4-nitro-3-(tetrahydro-2H-pyran-4-yloxy)phenoxy]pyridineYield 99.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-(5-fluoro-2-nitrophenoxy)tetrahydro-2H-pyran (13.6 g) and 6-[(methylsulfonyl)methyl]pyridin-3-ol (13.9 g) in N,N-dimethylformamide (300 mL) was added potassium carbonate (39 g), and the mixture was stirred at 110° C. for 2 hr. 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 50:50, volume ratio) to give the title compound (23 g, yield 95%) 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-e95e18d375c14e71b7b563f0cea6476c
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08557805B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes