Propargyl alcohol → HCID 86709263, compound

HRID 1050630Notes

Reaction equation

[CH2:1]([OH:4])[C:2]#[CH:3].[CH2:5]([O:7][P:8]([CH:13]([F:19])[C:14](OCC)=[O:15])([O:10][CH2:11][CH3:12])=[O:9])[CH3:6]>CCO.CCO.CCO.CCO.[Ti]>[CH2:5]([O:7][P:8]([CH:13]([F:19])[C:14]([O:4][CH2:1][C:2]#[CH:3])=[O:15])([O:10][CH2:11][CH3:12])=[O:9])[CH3:6]

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

temperatureheated
customSubsequently, ethanol and propargyl alcohol were evaporated away under reduced pressure at a temperature
customfalling within a range of from 70° C. to 100° C.
temperaturethe residue was cooled down to room temperature
addition0.18 g of water was added to the reaction liquid
filtrationthe formed precipitate was filtered away
customthe filtrate was purified through silica gel column chromatography (ethyl acetate/hexane=1/1 for elution)

Sources & evidence

ORD record: ord-ef6939a5aff54027bf67c7fa78023388
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09384906B2

Reaction notes

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