Reaktion #1137812

Reaktionsgleichung

propargyl alcohol

ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate

→

2-propynyl 2-(diethoxyphosphoryl)-2-fluoroacetate

Ausbeute 86.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   SonstigeSubsequently, ethanol and propargyl alcohol were evaporated away under reduced pressure at a temperature
3. 3
   Sonstigefalling within a range of from 70° C. to 100° C.
4. 4
   Temperaturthe residue was cooled down to room temperature
5. 5
   workup.ADDITION0.18 g of water was added to the reaction liquid
6. 6
   Filtrationthe formed precipitate was filtered away
7. 7
   Sonstigethe filtrate was purified through silica gel column chromatography (ethyl acetate/hexane=1/1 for elution)

Vorschrift

45.31 g (826 mmol) of propargyl alcohol and 0.94 g (4.1 mmol of tetraethyl titanate were added to 10.00 g (41.3 mmol) of ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate, and heated under reflux at 100° C. for 10 hours. Subsequently, ethanol and propargyl alcohol were evaporated away under reduced pressure at a temperature falling within a range of from 70° C. to 100° C., taking 10 hours, and then the residue was cooled down to room temperature. 0.18 g of water was added to the reaction liquid, the formed precipitate was filtered away, and the filtrate was purified through silica gel column chromatography (ethyl acetate/hexane=1/1 for elution) to give 8.96 g (yield 86%) of the intended 2-propynyl 2-(diethoxyphosphoryl)-2-fluoroacetate. The obtained 2-propynyl 2-(diethoxyphosphoryl)-2-fluoroacetate was analyzed through 1H-NMR to confirm the structure thereof. The results are shown below.

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