Methyl iodide → HCID 66967816, compound

HRID 70731Notes

Reaction equation

HRID 70731 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:9]=[C:8]([C:10]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[OH:22].[CH3:23]I>CN(C=O)C>[I:3][C:4]1[CH:9]=[C:8]([C:10]2([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[CH:7]=[CH:6][C:5]=1[O:22][CH3:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11703564HCID 11703564, compound

Product 1

HCID 66967816HCID 66967816, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% in mineral oil, 60 mg, 1.50 mmol) was added an ice-cooled solution of 2-iodo-4-(1-phenyl-cyclohexyl)-phenol (400 mg, 1.06 mmol) in DMF (10 mL). Methyl iodide (125 μL, 2.0 mmol) was added. The reaction temperature was allowed to reach room temperature. The mixture was stirred for 2 h, then quenched with water 10 mL and extracted with dichloromethane (2×20 mL). The combined organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was taken up in water (20 mL) and extracted with dichloromethane. The organic phase was dried (Na2SO4) and concentrated in vacuo. 1H-nmr of the syrup (430 mg) indicated full conversion to the methyl ether. 1H NMR (400 MHz, CDCl3): 7.71 (d, 1H, J=2.1 Hz), 7.32-7.25 (m, 4H), 7.18 (dd, 1H, J=2.1 Hz, J=8.8 Hz), 7.17-7.13 (m, 1H), 6.72 (d, 1H, J=8.8 Hz), 3.83 (s, 3H), 2.32-2.18 (m, 4H), 1.62-1.44 (m, 6H).

Workup

  1. customto reach room temperature
  2. customquenched with water 10 mL
  3. extractionextracted with dichloromethane (2×20 mL)
  4. dry with materialThe combined organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5a253ba51804dada1ab82c1330e0cec
Source dataset
uspto-grants-2014_09
Patent number
US08822548B2

Reaction notes

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