Hydroquinone → HCID 70558999, compound

HRID 707692Notes

Reaction equation

HRID 707692 reaction equation
[F:1][CH2:2][C@@H:3]([O:6][CH2:7][C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])=[N:9][OH:10])[CH:4]=[CH2:5].C1(C=CC(O)=CC=1)O>>[F:1][CH2:2][C@@H:3]1[C@@H:4]2[C@@:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])([NH:9][O:10][CH2:5]2)[CH2:7][O:6]1

Participants

3

Reactant 2

HCID 785HydroquinoneHCID 86724402HCID 86724402, compound

Product 1

HCID 70558999HCID 70558999, compoundYield 75%

Conditions

Temperature
145 °C

Procedure

(S)-2-((1-fluorobut-3-en-2-yl)oxy)-1-(2-fluorophenyl)ethanone oxime (67.5 g, 279.81 mmol) was dissolved in xylenes (560 mL) and hydroquinone (5.54 g, 50.36 mmol) was added. The reaction mixture was heated to reflux (heating block temperature 145° C.) for 5 hrs. The reaction was cooled to RT and the solvent was evaporated. The residue was purified by column chromatography on amino silica (30% EtOAc in hexanes) to obtain the title compound as a yellow oil (50.53 g, 75%). 1H NMR (400 MHz, CDCl3) δ ppm 3.32-3.42 (m, 1H) 3.96 (dd, J=10.11, 1.52 Hz, 2H) 4.16-4.43 (m, 2H) 4.44-4.83 (m, 2H) 5.38 (s, 1H) 7.09 (dd, J=11.75, 8.72 Hz, 1H) 7.18 (td, J=7.58, 1.26 Hz, 1H) 7.28-7.34 (m, 1H) 7.71 (br. s., 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction was cooled to RT
  4. customthe solvent was evaporated
  5. customThe residue was purified by column chromatography on amino silica (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d7ea9a598d464285b9d0b1e23afafd08
Source dataset
uspto-grants-2015_11
Patent number
US09175013B2

Reaction notes

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