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

HRID 2244865Notes

Reaction equation

HRID 2244865 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

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.

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

Sources & evidence

ORD record
ord-1f2b7e6b55d04afaa0f8d4f1c625bfc8
Source dataset
uspto-grants-2010_03
Patent number
US07678926B2

Reaction notes

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