Aluminium lithium hydride → Benzaldehyde, 3-ethoxy-5-(2,2,2-trifluoroethoxy)-

HRID 1990818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1990818
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[CH:7]=[C:6]([O:16][CH2:17][CH3:18])[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.O=[Mn]=O>[CH2:17]([O:16][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH2:11][C:12]([F:13])([F:14])[F:15])[CH:7]=1)[CH:3]=[O:2])[CH3:18]

Komponenten

5

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 68699922HCID 68699922, Verbindung

Produkt 1

HCID 58706345Benzaldehyde, 3-ethoxy-5-(2,2,2-trifluoroethoxy)-Ausbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-ethoxy-5-(2,2,2-trifluoro-ethoxy)-benzoic acid methyl ester (0.8 g, 2.88 mmol, 1.0 equiv) in anhydrous THF (20 mL) was added lithium aluminium hydride (0.273 g, 7.19 mmol, 2.5 equiv) and the reaction mixture stirred at rt for 4 h. The crude reaction mixture was filtered over Hyflo Super Cel, the filtrate extracted with diethyl ether (3×50 mL) and the combined organic phases dried over MgSO4 providing 0.75 g (99%) of the benzyl alcohol. The crude reaction product (0.75 g, 3.0 mmol, 1.0 equiv) was dissolved in THF (20 mL) and activated MnO2 (2.61 g, 30.00 mmol, 10.0 equiv) was added. After stirring at rt for 3 h, the reaction mixture was filtered over Hyflo Super Cel and the solvent removed by evaporation under reduced pressure. A conc. solution of sodium chloride (100 mL) was added, the mixture extracted with ethyl acetate (3×100 mL) and the combined organic phases dried over MgSO4. Purification of the crude material with column chromatography on silica eluting with heptane/ethyl acetate (4:1) provided 0.54 g (72%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.35 (t, J=7.0 Hz, 3H), 4.00 (q, J=7.0 Hz, 2H), 4.31 (q, J=8.1 Hz, 2H), 6.66-6.67 (m, 1H), 6.91-6.92 (m, 1H), 6.99-7.00 (m, 1H).

Aufarbeitung

  1. customThe crude reaction mixture
  2. filtrationwas filtered over Hyflo Super Cel
  3. extractionthe filtrate extracted with diethyl ether (3×50 mL)
  4. dry with materialthe combined organic phases dried over MgSO4 providing 0.75 g (99%) of the benzyl alcohol
  5. stirringAfter stirring at rt for 3 h
  6. filtrationthe reaction mixture was filtered over Hyflo Super Cel
  7. customthe solvent removed by evaporation under reduced pressure
  8. additionA conc. solution of sodium chloride (100 mL) was added
  9. extractionthe mixture extracted with ethyl acetate (3×100 mL)
  10. dry with materialthe combined organic phases dried over MgSO4
  11. customPurification of the crude material with column chromatography on silica eluting with heptane/ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-2a05353f4ad94ab8a89e574341178120
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645753B2

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