Methyl iodide → 1,1,5-Trimethoxy-2,6-dimethylheptane

HRID 1974190Notes

Reaction equation

HRID 1974190 reaction equation
[H-].[Na+].[CH3:3][O:4][CH:5]([O:15][CH3:16])[CH:6]([CH3:14])[CH2:7][CH2:8][CH:9]([OH:13])[CH:10]([CH3:12])[CH3:11].[H][H].[CH3:19]I>O1CCCC1.O.CN(C)P(=O)(N(C)C)N(C)C>[CH3:16][O:15][CH:5]([O:4][CH3:3])[CH:6]([CH3:14])[CH2:7][CH2:8][CH:9]([O:13][CH3:19])[CH:10]([CH3:12])[CH3:11]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 213991627,7-Dimethoxy-2,6-dimethylheptan-3-olHCID 178418361HCID 178418361, compound

Product 1

HCID 213990641,1,5-Trimethoxy-2,6-dimethylheptane

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

To a mixture of 2.4 g. of clean sodium hydride in 200 ml. of dry tetrahydrofuran containing 20 ml. of dry HMPT (hexamethylphosphorictriamide) is added dropwise a solution of 20.4 g. of 1,1-dimethoxy-5-hydroxy-2,6-dimethylheptane in dry tetrahydrofuran. The mixture is stirred at room temperature until evolution of hydrogen ceases and then 16 g. of methyl iodide is added. The reaction mixture is refluxed for 3 hours and then cooled, diluted with water and extracted with ether. The etheral extracts are evaporated under reduced pressure to yield crude 1,1,5-trimethoxy-2,6-dimethylheptane which can be purified by distillation or chromatography on Florisil.

Workup

  1. additionTo a mixture of 2.4 g
  2. temperatureThe reaction mixture is refluxed for 3 hours
  3. temperaturecooled
  4. extractionextracted with ether
  5. customThe etheral extracts are evaporated under reduced pressure

Sources & evidence

ORD record
ord-eba551d1be764852861edc74e52f0edd
Source dataset
uspto-grants-1976_12
Patent number
US04000174

Reaction notes

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