Trimethylsilylacetylene → 2-(1,3-Oxazol-4-yl)but-3-yn-2-ol

HRID 1398526Notes

Reaction equation

HRID 1398526 reaction equation
C([Li])CCC.[C:6]([Si](C)(C)C)#[CH:7].[O:12]1[CH:16]=[C:15]([C:17](=[O:19])[CH3:18])[N:14]=[CH:13]1>C1COCC1.O>[O:12]1[CH:16]=[C:15]([C:17]([OH:19])([C:6]#[CH:7])[CH3:18])[N:14]=[CH:13]1

Participants

6

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 222208751-(1,3-Oxazol-4-yl)ethan-1-oneHCID 178418339Butyllithium

Product 1

HCID 866695772-(1,3-Oxazol-4-yl)but-3-yn-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of n-butyllithium (2.5M in hexane, 1.03 mL, 2.57 mmol) in THF (3 mL) at −78° C. was added dropwise ethynyl(trimethyl)silane (0.34 mL, 2.38 mmol). The reaction was stirred at −78° C. for 10 minutes and then 1-(1,3-oxazol-4-yl)ethanone (220 mg, 1.98 mmol) was added in more THF (2 mL). The reaction was stirred at −78° C. to RT for 1 hr. The mixture was then diluted with water and the volatiles removed. The product was then extracted with EtOAc (2×15 mL) and the combined organics washed with water (2×5 mL) and dried (Na2SO4), filtered and concentrated in vacuo. The crude material was purified by column chromatography (eluted with 2-13% methanol) to give the title compound; 1H NMR (500 MHz, CDCl3) delta 1.85 (3H, s), 2.61 (1H, s), 2.92 (1H, s), 7.71 (1H, s), 7.87 (1H, s).

Workup

  1. stirringThe reaction was stirred at −78° C. to RT for 1 hr
  2. customthe volatiles removed
  3. extractionThe product was then extracted with EtOAc (2×15 mL)
  4. washthe combined organics washed with water (2×5 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by column chromatography (eluted with 2-13% methanol)

Sources & evidence

ORD record
ord-22fdebd2d78c40fbbd0367e014e26865
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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