Triacetoxyperiodinane → 4-Benzyloxyphenylacetaldehyde

HRID 62855

Reaktionsgleichung

Reaktionsgleichung von HRID 62855
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]=[O:17])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 3017260p-(Benzyloxy)phenethyl alcohol

Produkt 1

HCID 114134894-BenzyloxyphenylacetaldehydeAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-(4-Benzyloxy-phenyl)-ethanol (0.64 g, 2.80 mmol) obtained in Step B was dissolved in DCM (10 mL), and Dess-Martin periodinane (2.38 g, 5.60 mmol) was added thereto. The reactant was stirred at room temperature for 2 hours, diluted with DCM, and washed with Na2S2O3.5H2O aqueous solution. The remained organic solution was dried with MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (eluent, EtOAc/Hex=1/5) to obtain the title compound (0.50 g, 79%).

Aufarbeitung

  1. washwashed with Na2S2O3.5H2O aqueous solution
  2. dry with materialThe remained organic solution was dried with MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (eluent, EtOAc/Hex=1/5)

Quellen und Nachweise

ORD-Eintrag
ord-c47e3fb21b794da6acbfe7bae25b1ab3
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447044B2

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