Water → tetrahydro-4-(4-iodophenyl)-4-methoxy-2H-pyran

HRID 1365625

Reaction equation

HRID 1365625 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:17]I.O>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:14][CH3:17])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57033480tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol

Product 1

HCID 57762532tetrahydro-4-(4-iodophenyl)-4-methoxy-2H-pyran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under an argon atmosphere, a solution of tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol (2.99 g) in anhydrous DMF (10 ml) was added dropwise to a suspension of sodium hydride (60 wt %) (432 mg) in anhydrous DMF (20 ml) at room temperature, and the resulting mixture was stirred at room temperature for 75 minutes. Methyl iodide (0.92 ml) was added dropwise to the reaction solution and the resulting mixture was stirred at room temperature for 8.5 hours. Water was added thereto and the resulting mixture was extracted twice with ethyl acetate. Organic layers were washed with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=10/1) to obtain tetrahydro-4-(4-iodophenyl)-4-methoxy-2H-pyran (2.87 g). NMR (H1, CDCl3): δ 1.90-2.02 (4H, m), 2.97 (3H, s), 3.80-3.88 (4H, m), 7.14 (1H, d, J=8.5 Hz), 7.70 (1H, d, J=8.5 Hz)

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 8.5 hours
  2. extractionthe resulting mixture was extracted twice with ethyl acetate
  3. washOrganic layers were washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing anhydrous sodium sulfate
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-07edcc1954074f03ac9015a722320025
Source dataset
uspto-grants-2011_02
Patent number
US07893046B2

Linked notes

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