2,6-Lutidine → (Diethoxyphosphoryl)methyl trifluoromethanesulfonate

HRID 1510333Notes

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. Within 1.5 hours the mixture is allowed to come up to 0° C. and then diluted with 300 ml cold diethyl ether. Any solids precipitated 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

customto come up to 0° C.
customAny solids precipitated
filtrationare 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-dee3de4979e042d4a20bcf823f92419f
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211923B2

Reaction notes

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