Tetrahydrofuran → 2,2-Dihydroxy-3'-(alpha,alpha,alpha-trifluoro-m-tolyloxy)acetophenone

HRID 1980115

Reaktionsgleichung

Reaktionsgleichung von HRID 1980115
CC(S(C(SC)C)=[O:6])SC.C([Li])CCC.[F:16][C:17]([F:34])([F:33])[C:18]1[CH:19]=[C:20]([CH:30]=[CH:31][CH:32]=1)[O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=[O:26].[O:35]1[CH2:39]CCC1>CCCCCC>[OH:6][CH:39]([OH:35])[C:25]([C:24]1[CH:27]=[CH:28][CH:29]=[C:22]([O:21][C:20]2[CH:19]=[C:18]([C:17]([F:33])([F:34])[F:16])[CH:32]=[CH:31][CH:30]=2)[CH:23]=1)=[O:26]

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 5227113-(3-(Trifluoromethyl)phenoxy)benzaldehydeHCID 86596509Methyl(methylthio)methylsulfoxideHCID 178418339Butyllithium

Produkt 1

HCID 204374692,2-Dihydroxy-3'-(alpha,alpha,alpha-trifluoro-m-tolyloxy)acetophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a stirred solution of 3.10 g of methyl methyl thiomethylsulfoxide in 20 ml of tetrahydrofuran under argon in an ice bath was added 10.4 ml. of 2.4M n-butyllithium in hexane via a syringe during 15 minutes, maintaining the temperature at 10°-15° C. The mixture was stirred at 10° C. for 10 minutes, then recooled and a solution of 5.32 g of m-[m-(trifluoromethyl)phenoxy]benzaldehyde in 10 ml of tetrahydrofuran was added during 10 minutes, maintaining the temperature at <10° C. The resulting solution was stirred at 0°-5° C. for one hour, then the tetrahydrofuran was evaporated. The resulting yellow foam was added to dimethyl sulfoxide and cooled in an ice bath while aqueous hydrobromic acid was added. The reaction was then heated at 50° C. overnight, then poured into ice and extracted with ethyl acetate. The extract was washed with water, saturated sodium bicarbonate and brine, dried and evaporated, giving 2,2-dihydroxy-3'-(α,α,α-trifluoro-m-tolyloxy)acetophenone as a yellow oil.

Aufarbeitung

  1. temperaturemaintaining the temperature at 10°-15° C
  2. temperaturemaintaining the temperature at <10° C
  3. stirringThe resulting solution was stirred at 0°-5° C. for one hour
  4. customthe tetrahydrofuran was evaporated
  5. additionThe resulting yellow foam was added to dimethyl sulfoxide
  6. temperaturecooled in an ice bath while aqueous hydrobromic acid
  7. additionwas added
  8. temperatureThe reaction was then heated at 50° C. overnight
  9. additionpoured into ice
  10. extractionextracted with ethyl acetate
  11. washThe extract was washed with water, saturated sodium bicarbonate and brine
  12. customdried
  13. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f915bf2641264d66840dd1e9225cd9b3
Quelldatensatz
uspto-grants-1984_11
Patentnummer
US04485114

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