Water → HCID 17904801, compound

HRID 1069682Notes

Reaction equation

HRID 1069682 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:11])[O:8][CH:7]([CH2:9][OH:10])[CH2:6][O:5]1.[CH2:12](Br)[C:13]#[CH:14].O>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:3][C:4]1([CH3:11])[O:8][CH:7]([CH2:9][O:10][C:12]#[C:13][CH3:14])[CH2:6][O:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 7528SolketalHCID 7842Propargyl bromideHCID 24758Sodium hydride

Product 1

HCID 17904801HCID 17904801, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (1.32 g, 55 mmol) was added to a solution of 2,2-dimethyl-1,3-dioxolane-4-methanol (Aldrich) in THF (60 mL), and the resulting mixture was heated at reflux for 90 min then cooled to 0° C. Tetrabutylammonium iodide (370 mg), and propargyl bromide (80% in toluene, 6.22 mL, 50 mmol) (Aldrich) were added successively. After stirring for 150 min. at room temperature, 20 mL water was added and the THF was evaporated in vacuo. The aqueous layer was then extracted with diethyl ether (4×50 mL), and the combined organic layers were dried over magnesium sulfate and concentrated in vacuo to yield rac-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyl-1-propyne.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 90 min
  3. customthe THF was evaporated in vacuo
  4. extractionThe aqueous layer was then extracted with diethyl ether (4×50 mL)
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19aa807c6bd54c178d6589efe98ca237
Source dataset
uspto-grants-2001_06
Patent number
US06252086B1

Reaction notes

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