2,6-Lutidine → (Diethoxyphosphoryl)methyl trifluoromethanesulfonate

HRID 1807437Notes

Reaction equation

[CH2:1]([O:3][P:4]([CH2:9]CO)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].N1C(C)=CC=CC=1C.[F:20][C:21]([F:34])([F:33])[S:22]([O:25]S(C(F)(F)F)(=O)=O)(=[O:24])=[O:23]>ClCCl.C(OCC)C>[F:20][C:21]([F:34])([F:33])[S:22]([O:25][CH2:9][P:4]([O:3][CH2:1][CH3:2])([O:5][CH2:6][CH3:7])=[O:8])(=[O:24])=[O:23]

Participants

Conditions

Temperature: -50 °C

Procedure

5.01 ml diethyl-(hydroxyethyl)-phosphonate are dissolved in 50 ml dichloromethane, combined with 4.42 ml of 2,6-lutidine and cooled to −50° C. Then a solution of 6 ml trifluoromethanesulphonic acid anhydride in 10 ml dichloromethane is slowly added dropwise. The mixture is allowed to come up to 0° C. within 1.5 hours and then diluted with 300 ml of cold diethyl ether. The precipitated solids are filtered off and the filtrate is washed twice with ice water, once with 1 N hydrochloric acid and once with saturated sodium chloride solution. After drying with sodium sulphate the solvents are eliminated in vacuo.

Workup

filtrationThe precipitated solids are filtered off
washthe filtrate is washed twice with ice water, once with 1 N hydrochloric acid and once with saturated sodium chloride solution
dry with materialAfter drying with sodium sulphate the solvents

Sources & evidence

ORD record: ord-4ffe84da72c1410a808b28b05147dac5
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357689B2

Reaction notes

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