Hydroxyamine hydrochloride → (S)-1-(2-fluorophenyl)-2-((1,1,1-trifluorobut-3-en-2-yl)oxy)ethanone oxime

HRID 1429609Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][O:10][C@@H:11]([CH:16]=[CH2:17])[C:12]([F:15])([F:14])[F:13].Cl.[NH2:20][OH:21].C([O-])(=O)C.[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:20][OH:21])[CH2:9][O:10][C@@H:11]([CH:16]=[CH2:17])[C:12]([F:15])([F:14])[F:13]

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-1-(2-Fluorophenyl)-2-((1,1,1-trifluorobut-3-en-2-yl)oxy)ethanone (41.22 g) was dissolved in anhydrous methanol (400 mL) and hydroxylamine hydrochloride (14.0 g) and sodium acetate (19.0 g) were added. The reaction mixture was heated to 50° C. for 90 min, then cooled to RT, concentrated in vacuo and the residue purified by silica gel chromatography (2% to 15% EtOAc in hexanes) to afford the title compound as a mixture of geometric isomers (40.54 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 4.04-4.15 (m, 0.8 H), 4.18-4.26 (m, 0.2 H), 4.44-4.57 (m, 0.4 H) 4.79-4.90 (m, 1.6 H) 5.37-5.56 (m, 2 H) 5.64-5.78 (m, 1 H) 7.03-7.26 (m, 2 H) 7.33-7.54 (m, 2 H), 7.90 (br s, 0.2H), 8.51 (br s, 0.8H).

Workup

temperaturecooled to RT
concentrationconcentrated in vacuo
customthe residue purified by silica gel chromatography (2% to 15% EtOAc in hexanes)

Sources & evidence

ORD record: ord-e66ac36133904b73972d1a9aafa19af0
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940734B2

Reaction notes

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