Methyl iodide → (+/-)-3,4-Dimethoxy-3-methylbut-1-yne

HRID 2042760Notes

Reaction equation

HRID 2042760 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][O:8][CH2:9][C:10]([CH3:14])([OH:13])[C:11]#[CH:12].CI>O1CCCC1.CCOCC.O>[CH3:1][O:13][C:10]([CH3:14])([CH2:9][O:8][CH3:7])[C:11]#[CH:12]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 217064261-Methoxy-2-methylbut-3-yn-2-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 86642359(+/-)-3,4-Dimethoxy-3-methylbut-1-yne

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

17.5 ml of the 1.0M solution of potassium tert-butoxide in tetrahydrofuran (Aldrich; 17.52 mmol) are added to a solution, cooled with an ice bath, of 2 g of (±)-1-methoxy-2-methyl-3-butyn-2-ol (17.52 mmol) in 6 ml of tetrahydrofuran. Stirring is carried out at ambient temperature for 30 minutes and then 0.55 ml of methyl iodide (35.04 mmol) is added. The reaction mixture is stirred at ambient temperature for 3 hours and then is diluted with ether and water. After separation by settling, the organic phase is washed with water, dried over sodium sulfate, filtered and concentrated under limited vacuum. 2.4 g of the expected product are obtained in the form of a yellow oil comprising residual ether and residual tetrahydrofuran. The (±)-3,4-dimethoxy-3-methylbut-1-yne obtained is used in the following stage without subsequent purification.

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 3 hours
  2. customAfter separation
  3. washthe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under limited vacuum

Sources & evidence

ORD record
ord-7534b0db98414c2e9deed18c8201aca1
Source dataset
uspto-grants-2013_11
Patent number
US08586602B2

Reaction notes

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