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

HRID 1429616Notes

Reaction equation

HRID 1429616 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][O:11][C@@H:12]([CH:17]=[CH2:18])[C:13]([F:16])([F:15])[F:14].Cl.[NH2:21][OH:22].C([O-])(=O)C.[Na+]>CO>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[N:21][OH:22])[CH2:10][O:11][C@@H:12]([CH:17]=[CH2:18])[C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 70497436(S)-1-(2,3-difluorophenyl)-2-((1,1,1-trifluorobut-3-en-2-yl)oxy)ethanone

Product 1

HCID 86668363(S)-1-(2,3-difluorophenyl)-2-((1,1,1-trifluorobut-3-en-2-yl)oxy)ethanone oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

(S)-1-(2,3-difluorophenyl)-2-((1,1,1-trifluorobut-3-en-2-yl)oxy)ethanone (3.91 g) was dissolved in anhydrous methanol (40 mL) and hydroxylamine hydrochloride (1.25 g) and sodium acetate (1.68 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 20% EtOAc in hexanes) to afford the title compound as a mixture of geometric isomers (4.10 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 4.04-4.26 (m 1 H), 4.43-4.55 (m, 0.4 H) 4.80-4.89 (m, 1.6 H) 5.39-5.55 (m, 2 H) 5.64-5.80 (m, 1 H) 7.05-7.30 (m, 3 H), 7.76 (br s, 0.2 H), 8.30 (br s, 0.8 H).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated in vacuo
  3. customthe residue purified by silica gel chromatography (2% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2fec6e49002c4495b478010648d6c84b
Source dataset
uspto-grants-2015_01
Patent number
US08940734B2

Reaction notes

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