(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid → Methyl 2-(4-(trifluoromethyl)phenyl)acetate

HRID 1475632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1475632
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[CH3:15][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO.C(OCC)C>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH3:15])=[O:11])=[CH:7][CH:8]=1

Komponenten

6

Edukt 2

HCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 167693Trimethylsilyldiazomethane

Produkt 1

HCID 12717573Methyl 2-(4-(trifluoromethyl)phenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

6.0 g (29.4 mmol) of [4-(trifluoromethyl)phenyl]acetic acid were dissolved in 67.1 ml of toluene and 46.2 ml of methanol, and 26.5 ml (52.9 mmol) of a 2 M solution of trimethylsilyldiazomethane in diethyl ether were added dropwise with cooling. After the addition had ended, cooling was removed and the mixture was stirred at RT for another 1 h, after which excess trimethylsilyldiazomethane was destroyed by addition of 2.0 ml of acetic acid. The reaction mixture was concentrated under reduced pressure and the crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 80:1). This gave 4.33 g of the target compound (67.6% of theory).

Aufarbeitung

  1. temperaturewith cooling
  2. additionAfter the addition
  3. temperaturecooling
  4. customwas removed
  5. customafter which excess trimethylsilyldiazomethane was destroyed by addition of 2.0 ml of acetic acid
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customthe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 80:1)

Quellen und Nachweise

ORD-Eintrag
ord-b4b7b6379ce24be7898de4d912699fac
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018258B2

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