Potassium Carbonate → (+/-)-2-Cyclopropyl-1-methoxybut-3-yn-2-ol

HRID 1260590Notes

Reaction equation

HRID 1260590 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([C:10]([OH:20])([C:14]#[C:15][Si](C)(C)C)[CH2:11][O:12][CH3:13])[CH2:9][CH2:8]1>CO>[CH:7]1([C:10]([OH:20])([C:14]#[CH:15])[CH2:11][O:12][CH3:13])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67081796HCID 67081796, compound

Product 1

HCID 80410057(+/-)-2-Cyclopropyl-1-methoxybut-3-yn-2-olYield 39.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10.9 mg of potassium carbonate (0.08 mmol) are added to a solution of 1.67 g of (±)-2-cyclopropyl-1-methoxy-4-(trimethylsilyl)but-3-yn-2-ol (7.86 mmol) in methanol, and the mixture is stirred overnight at ambient temperature. The methanol is evaporated off and the residue is taken up with an ethyl acetate/water mixture. The product is extracted 3 times with ethyl acetate and the organic phases are then combined, dried over sodium sulphate, filtered, and concentrated under vacuum. 0.434 g of (±)-2-cyclopropyl-1-methoxybut-3-yn-2-ol is obtained in the form of an oil used without subsequent purification (crude yield=40%).

Workup

  1. customThe methanol is evaporated off
  2. extractionThe product is extracted 3 times with ethyl acetate
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-572faae8c5eb4b1eb04d2eedc94e2842
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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