Ethanol → 3-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid ethyl ester

HRID 729367Notes

Reaction equation

[CH2:1]([O:8][N:9]=[CH:10][C:11]1[C:12]([F:22])=[C:13]([CH:17]=[C:18]([F:21])[C:19]=1[F:20])[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23](O)[CH3:24].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:23]([O:15][C:14](=[O:16])[C:13]1[CH:17]=[C:18]([F:21])[C:19]([F:20])=[C:11]([CH:10]=[N:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:12]=1[F:22])[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid (0.117 g, 0.378 mmol), 4-dimethylaminopyridine (0.023 g, 0.189 mmol), anhydrous ethanol (0.030 mL, 0.517 mmol) are mixed in dichloromethane (6 mL), cooled to 0° C., and treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.082 g, 0.427 mmol). After 2 hours at 0° C. and room temperature for 21 hours, the solvents are evaporated. The residue is dissolved in chloroform, washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by chromatography (1:8 ethyl acetate/hexanes) provided the title compound (0.068 g). 1H NMR (200 MHz, CDCl3): δ 8.27 (s, 1H), 7.87-7.66 (m, 1H), 7.49-7.28 (m, 5H), 5.27 (s, 2H), 4.48-4.29 (q, 2H), 1.46-1.31 (t, 3H).

Workup

waitroom temperature for 21 hours
customthe solvents are evaporated
dissolutionThe residue is dissolved in chloroform
washwashed with saturated NaHCO3 and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by chromatography (1:8 ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-d44ea83c7e33403298dea66b479b0a7a
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582627B2

Reaction notes

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