Ethyl Acetate → HCID 67081796, compound

HRID 1260589Notes

Reaction equation

HRID 1260589 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH3:6][O:7][CH2:8][C:9](=[O:16])[C:10]#[C:11][Si:12]([CH3:15])([CH3:14])[CH3:13].C(OCC)(=O)C>CCOCC>[CH:1]1([C:9]([OH:16])([C:10]#[C:11][Si:12]([CH3:13])([CH3:15])[CH3:14])[CH2:8][O:7][CH3:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 858600211-methoxy-4-(trimethylsilyl)-3-Butyn-2-oneHCID 178418630HCID 178418630, compound

Product 1

HCID 67081796HCID 67081796, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

52.85 ml of 0.5 M cyclopropylmagnesium bromide (26.43 mmol, Aldrich) are added to a solution of 3 g of 1-methoxy-4-(trimethylsilyl)but-3-yn-2-one (17.62 mmol) in 160 ml of ether. The mixture is stirred at ambient temperature overnight and is then cooled with a water/ice bath and a solution of NH4Claq and ethyl acetate is added. The mixture is extracted 3 times with ethyl acetate and the organic phases are then combined, dried over sodium sulphate, filtered, and concentrated under vacuum. The oily residue is purified by silica column chromatography, elution being carried out with a cyclohexane:ethyl acetate gradient, 100:0 to 80:20, so as to obtain 1.9 g of (±)-2-cyclopropyl-1-methoxy-4-(trimethylsilyl)but-3-yn-2-ol in the form of an oil, with a yield of 51%.

Workup

  1. temperatureis then cooled with a water/ice bath
  2. extractionThe mixture is extracted 3 times with ethyl acetate
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe oily residue is purified by silica column chromatography, elution

Sources & evidence

ORD record
ord-06c145b62af446589c20bc403f0255fd
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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