Water → 13580-09-1

HRID 366660Notes

Reaction equation

HRID 366660 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][CH2:14][C:13]#[CH:12])[CH2:6][O:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 7528SolketalHCID 7842Propargyl bromideHCID 24758Sodium hydride

Product 1

HCID 342926213580-09-1

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)methoxy]-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-bc2ce374022e441bab99be40a30d8745
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

Loading…