Cesium carbonate → 4-(3-methoxy-4-nitrophenoxy)tetrahydro-2H-pyran

HRID 417312Notes

Reaction equation

HRID 417312 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].C([O-])([O-])=O.[Cs+].[Cs+].[O:19]1[CH2:24][CH2:23][CH:22](OS(C)(=O)=O)[CH2:21][CH2:20]1>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[O:12][CH:22]1[CH2:23][CH2:24][O:19][CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11344352Oxan-4-yl methanesulfonateHCID 129005323-Methoxy-4-nitrophenol

Product 1

HCID 592846694-(3-methoxy-4-nitrophenoxy)tetrahydro-2H-pyranYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Step B To a solution of 3-methoxy-4-nitrophenol (0.5 g, 3 mmol) prepared in Example 132 Step A in anhydrous DMF (13 mL) were added Cs2CO3 (2.9 g, 8.9 mmol) and methanesulfonic acid tetrahydropyran-4-yl ester (0.64 g, 3.6 mmol) sequentially. The reaction mixture was heated at 120° C. for 3 h. The mixture was cooled to room temperature, and diluted with water. The mixture was extracted with ethyl acetate three times. The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (40-60% EtOAc in hexanes) to give 4-(3-methoxy-4-nitrophenoxy)tetrahydro-2H-pyran as a yellow oil (0.4 g, 53%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate three times
  3. extractionThe combined organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (40-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9fc16bb9ca28444ea4c36b87fa98636e
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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