Pyrrolidine → 6,8-Difluoro-2,2-bis(fluoromethyl)chroman-4-one

HRID 536445

Reaktionsgleichung

Reaktionsgleichung von HRID 536445
[F:1][C:2]1[C:3]([OH:12])=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[F:13][CH2:14][C:15]([CH2:17][F:18])=O.N1CCCC1>CO>[F:8][C:6]1[CH:5]=[C:4]2[C:3](=[C:2]([F:1])[CH:7]=1)[O:12][C:15]([CH2:17][F:18])([CH2:14][F:13])[CH2:10][C:9]2=[O:11]

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 2283971,3-DifluoroacetoneHCID 27369761-(3,5-Difluoro-2-hydroxyphenyl)ethan-1-one

Produkt 1

HCID 673622886,8-Difluoro-2,2-bis(fluoromethyl)chroman-4-oneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1-(3,5-difluoro-2-hydroxyphenyl)ethanone (4.98 g, 28.9 mmol), MeOH (50 mL), 1,3-difluoroacetone (5.44 g, 57.9 mmol), and pyrrolidine (4.79 mL, 57.9 mmol) was heated at 60° C. for 20 hours. The dark solution was cooled, concentrated, chased with toluene, and then passed through a silica gel plug, washing with toluene (200 mL) and MTBE (200 mL). The filtrate was washed with 2N NaOH (50 mL×2), dried (Na2SO4), filtered, and concentrated to afford the title compound (5.80 g, 23.37 mmol, 81%), which was used without further purification in the next step. MS (DCI) m/z 299 (M+51)+.

Aufarbeitung

  1. temperatureThe dark solution was cooled
  2. concentrationconcentrated
  3. washwashing with toluene (200 mL) and MTBE (200 mL)
  4. washThe filtrate was washed with 2N NaOH (50 mL×2)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-81239152b40e4860b3421bf00904adf5
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859584B2

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