Hydroquinone → HCID 67610270, compound

HRID 2281855Notes

Reaction equation

HRID 2281855 reaction equation
FC1C=CC=CC=1[C:8](=[N:18][OH:19])[CH2:9][O:10][C@@H:11]([CH:16]=[CH2:17])[C:12]([F:15])([F:14])[F:13].C1(C=CC(O)=CC=1)O>>[F:15][C:12]([F:13])([F:14])[C@@H:11]1[C@@H:16]2[C:8](=[N:18][O:19][CH2:17]2)[CH2:9][O:10]1

Participants

3

Reactant 2

HCID 785HydroquinoneHCID 86668362(S)-1-(2-fluorophenyl)-2-((1,1,1-trifluorobut-3-en-2-yl)oxy)ethanone oxime

Product 1

HCID 67610270HCID 67610270, compoundYield 108.6%

Conditions

Temperature
140 °C

Procedure

(S)-1-(2-Fluorophenyl)-2-((1,1,1-trifluorobut-3-en-2-yl)oxy)ethanone oxime (40.54 g) was dissolved in xylenes (400 mL) and hydroquinone (4.0 g) was added. The reaction mixture was heated to reflux (heating block temperature 140° C.) for 22 hrs, then cooled and evaporated. The residue was purified by silica gel column chromatography (1% to 30% EtOAc in hexanes) to obtain the title compound (28.76 g). 1H NMR (400 MHz, CDCl3) δ ppm: 3.71-3.81 (m, 1H), 4.04-4.35 (m, 3H), 4.51-4.62 (m, 1H), 5.38-5.54 (m, 1H), 7.07-7.26 (m, 2H), 7.32-7.42 (m, 1H), 7.54-7.67 (m, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturecooled
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (1% to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-677d157456754b0a80b09d4b39fe4c65
Source dataset
uspto-grants-2015_09
Patent number
US09139594B2

Reaction notes

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