Methyl iodide → HCID 178500706, compound

HRID 420764Notes

Reaction equation

HRID 420764 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C@H:5]1[CH2:10][CH2:9][C@@H:8]([OH:11])[CH2:7][CH2:6]1.[H-].[Na+].I[CH3:16]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C@H:5]1[CH2:10][CH2:9][C@@H:8]([O:11][CH3:16])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178500704HCID 178500704, compound

Product 1

HCID 178500706HCID 178500706, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
2.5 °C

Procedure

Cis (4-Hydroxy-cyclohexyl)-acetic acid methyl ester (500 mg, 2.90 mmol) were dissolved in 1.5 ml DMF and cooled to 0-5° C. Sodium hydride (190 mg, 4.35 mmol, 55%) and iodomethane (3.62 ml, 23.2 mmol) were added and the reaction mixture stirred for 4 hours at 0-5° C. The reaction mixture was quenched with saturated NaHCO3-solution and extracted with dichloromethane. The organic extract was washed with brine, dried with sodium sulfate, filtered and evaporated. The crude product (561 mg, quant.) was obtained as a colourless oil and used without any further purification for the next step.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3-solution
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0941b75f8abf4f65af15e8bfaaf31125
Source dataset
uspto-grants-2012_01
Patent number
US08097637B2

Reaction notes

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