Methyl iodide → 4-Ethylsulfanyl-3-methoxy-3-methyl-but-1-yne
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
Product 1
Reagents, catalysts & solvents 1
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
- additionThe mixture was poured onto water
- extractionextracted twice with diethyl ether
- washThe diethyl ether extracts were washed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- 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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