Triacetoxyperiodinane → 3-(1-tert-butoxycarbonyl-Benzimidazol-2-yl)propionaldehyde

HRID 747295

Reaktionsgleichung

Reaktionsgleichung von HRID 747295
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][CH2:18][CH2:19][OH:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][CH2:18][CH:19]=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 220186013-(1-tert-butoxycarbonyl-Benzimidazol-2-yl)propan-1-ol

Produkt 1

HCID 220187793-(1-tert-butoxycarbonyl-Benzimidazol-2-yl)propionaldehydeAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-(1-tert-butoxycarbonyl-Benzimidazol-2-yl)propan-1-ol (186 mg, 0.67 mmol) in CH2Cl2 (4 mL) was added Dess-Martin reagent (314 mg, 0.74 mmol) and the resulting mixture was allowed to stir at room temperature under N2 for 1 hour. The mixture was further diluted with 300-mL ethyl acetate, and washed with 1N NaOH, brine and dried over Na2SO4. Evaporation of the solvent and flash chromatograph of residue over silica gel, using 20% ethyl acetate in CH2Cl2, gave the title compound (141 mg, 76%) as pure white solid. 1H NMR (CDCl3) □ 1.72 (s, 9H), 3.13 (t, 2H, J=6.8 Hz), 3.52 (t, 2H, J=6.8 Hz), 7.28-7.34 (m, 2H), 7.66-7.67 (m, 1H), 7.87-7.91 (m, 1H), 9.97 (s, 1H).

Aufarbeitung

  1. washwashed with 1N NaOH, brine
  2. dry with materialdried over Na2SO4
  3. customEvaporation of the solvent and flash chromatograph of residue over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d65a2619f7d54355aa932c1ee8d8e998
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396840B2

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