Methyl iodide → 4-Ethylsulfanyl-3-methoxy-3-methyl-but-1-yne

HRID 1182192Notes

Reaction equation

HRID 1182192 reaction equation
[CH2:1]([S:3][CH2:4][C:5]([CH3:9])([OH:8])[C:6]#[CH:7])[CH3:2].[H-].[Na+].I[CH3:13]>CN(C)C=O>[CH2:1]([S:3][CH2:4][C:5]([O:8][CH3:13])([CH3:9])[C:6]#[CH:7])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 589795961-Ethylsulfanyl-2-methyl-but-3-yn-2-ol

Product 1

HCID 589796044-Ethylsulfanyl-3-methoxy-3-methyl-but-1-yne

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Ethylsulfanyl-2-methyl-but-3-yn-2-ol (0.29 g, 2.0 mmol) was added to a mixture of sodium hydride (60% dispersion in mineral oil, 88 mg, 2.2 mmol) in dimethylformamide (5 mL) under argon. Iodomethane (0.12 mL, 2.0 mmol) was then added to the reaction mixture via syringe and the mixture allowed to stir overnight. The mixture was poured onto water and extracted twice with diethyl ether. The diethyl ether extracts were washed with water and brine, dried over magnesium sulfate, filtered, and evaporated to yield a yellow oil. The oil was purified by column chromatography eluting with dichloromethane to yield the title compound as a clear liquid.

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted twice with diethyl ether
  3. washThe diethyl ether extracts were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a yellow oil
  8. customThe oil was purified by column chromatography
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-cca5fe2167eb4fc4b33c46c674128898
Source dataset
uspto-grants-2007_10
Patent number
US07288553B2

Reaction notes

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