Methyl iodide → HCID 44722430, compound

HRID 2192295Notes

Reaction equation

HRID 2192295 reaction equation
[C:1]1([C:7]2([OH:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:18]>O1CCCC1>[CH3:18][O:14][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 16385Cycloheptanol, 1-phenyl-HCID 24758Sodium hydride2×

Product 1

HCID 44722430HCID 44722430, compoundYield 138.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1-Phenyl-cycloheptanol (Example 1a) (7.6 g) was dissolved in tetrahydrofuran (100 mL) and sodium hydride (60% in oil, 2.0 g) added. The reaction was stirred at 60° C. for 5 minutes and iodomethane (7.1 g) added. The mixture was maintained at 60° C. overnight and then further quantities of sodium hydride (60% in oil, 2.0 g) and iodomethane (7.1 g) were added and the reaction was refluxed for 70 hours. The reaction mixture was partitioned between water (100 mL) and isohexane (100 mL) and the organic layer separated, dried (MgSO4) and evaporated to afford the sub-titled compound (11.31 g).

Workup

  1. temperatureThe mixture was maintained at 60° C. overnight
  2. temperaturethe reaction was refluxed for 70 hours
  3. customThe reaction mixture was partitioned between water (100 mL) and isohexane (100 mL)
  4. customthe organic layer separated
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-dbd995c6d6b54729bd11747b9fd8a50e
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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