4-Hydroxybenzaldehyde → 4-(3,3,3-Trifluoropropoxy)benzaldehyde

HRID 339510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339510
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][C:11]([F:16])([F:15])[CH2:12][CH2:13]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:10][C:11]([F:16])([F:15])[CH2:12][CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 1375123,3,3-Trifluoro-1-propanolHCID 5363146Diisopropyl azodicarboxylate

Produkt 1

HCID 583421884-(3,3,3-Trifluoropropoxy)benzaldehydeAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-hydroxybenzaldehyde (0.36 g, 2.93 mmol), 3,3,3-trifluoropropanol (0.5 g, 4.39 mmol) and triphenylphosphine (1.15 g, 4.39 mmol) in dry THF (10 ml) at 0° C. under an atmosphere of argon was added dropwise diisopropylazodicarboxylate (0.89 g, 4.39 mmol). On completion of the addition, the reaction mixture was stirred at room temperature for 60 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (4:1 Hexane/EtOAc) to give the title compound (0.25 g, 46%) as a colourless solid.

Aufarbeitung

  1. additionOn completion of the addition
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by flash chromatography (4:1 Hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-30640eb58511495b83faa2a0fcf20d35
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895313B2

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