Diisobutylaluminum hydride → 4-(Oxazol-2-yl)-benzyl alcohol

HRID 1157915

Reaktionsgleichung

Reaktionsgleichung von HRID 1157915
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:5]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[O:11]1[CH:12]=[CH:13][N:14]=[C:10]1[C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 21985208Methyl 4-(oxazol-2-yl)benzoate

Produkt 1

HCID 207256244-(Oxazol-2-yl)-benzyl alcoholAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of methyl-4-(oxazol-2-yl)-benzoate (0.203 g, 1 mmol) in CH2Cl2 (10 mL) 0° C. was added DIBAL-H (4 mL of a 1.0M solution in dichloromethane, 4 mmol) over 10 minutes. The resultant solution was stirred at 0° C. for 2 hours then quenched with an aqueous saturated solution of sodium potassium tartrate (20 mL) and the biphasic mixture stirred rapidly for 60 minutes. The phases were separated and the aqueous layer extracted with CH2Cl2 (3×10 mL). The combined organic fractions were dried (Na2SO4), filtered, concentrated and purified by chromatography on silica gel (10:1 CH2Cl2/MeOH) to afford the title alcohol (0.156 g, 89%). 1H NMR (CDCl3) δ 3.42 (t, 1H, J=6.0 Hz (OH)), 4.77 (s, 2H, J=6.0 Hz), 7.24 (s, 1H), 7.47 (d, 2H, J=7.8 Hz), 7.71 (s, 1H), 8.05 (d, 2H, J=7.8 Hz).

Aufarbeitung

  1. customthen quenched with an aqueous saturated solution of sodium potassium tartrate (20 mL)
  2. customThe phases were separated
  3. extractionthe aqueous layer extracted with CH2Cl2 (3×10 mL)
  4. dry with materialThe combined organic fractions were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by chromatography on silica gel (10:1 CH2Cl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-fca2cf1652574978b28ecc67be6d7456
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807694B2

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