Trifluoroacetic acid → 4-(2-{[Ethoxy(methyl)phosphoryl]oxy}ethyl)benzoic acid

HRID 1013521Notes

Reaction equation

HRID 1013521 reaction equation
[CH2:1]([O:3][P:4]([O:7][CH2:8][CH2:9][C:10]1[CH:22]=[CH:21][C:13]([C:14]([O:16]C(C)(C)C)=[O:15])=[CH:12][CH:11]=1)([CH3:6])=[O:5])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][P:4]([O:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:21][CH:22]=1)([CH3:6])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57925877Tert-butyl 4-(2-{[ethoxy(methyl)phosphoryl]oxy}ethyl)benzoate

Product 1

HCID 579259664-(2-{[Ethoxy(methyl)phosphoryl]oxy}ethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-{[ethoxy(methyl)phosphoryl]oxy}ethyl)benzoate (108 mg, 0.33 mmol) in DCM (0.66 mL) was added TFA (0.60 mL, 7.8 mmol). After stirring at room temperature for 30 minutes, the solution was concentrated in vacuo to give the title compound as a colorless oil. 1H NMR (CDCl3, 600 MHz) δ 7.85 (d, J=8.2 Hz, 2H), 7.37 (d, J=8.2 Hz, 2H), 4.10-4.16 (m, 2H), 3.80-3.88 (m, 2H), 2.95 (t, J=6.4 Hz, 2H), 1.32 (d, J=17.3 Hz, 3H), 1.13 (t, J=7.1 Hz, 3H). MS cal'd 272 (MH+), exp 272 (MH+).

Workup

  1. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-f3ffcfecd2ee481c9878152b032205bf
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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