Triacetoxyperiodinane → 3-(Benzyloxy)-2-methylbenzaldehyde

HRID 1964942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1964942
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[C:11]([CH2:15][OH:16])[CH:12]=[CH:13][CH:14]=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>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH:15]=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 58087471(3-Benzyloxy-2-methyl-phenyl)-methanol

Produkt 1

HCID 159481993-(Benzyloxy)-2-methylbenzaldehydeAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (3-benzyloxy-2-methyl-phenyl)-methanol (622, 627 mg, 2.75 mmol) in tetrahydrofuran (60 mL) was added Dess-Martin periodinane (2.9 g, 6.87 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 50 minutes. The reaction mixture was quenched with a solution of saturated sodium thiosulfate, extracted with ethyl acetate, washed with sodium bicarbonate, brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a white solid (623, 0.55 g, 84%).

Aufarbeitung

  1. customThe reaction mixture was quenched with a solution of saturated sodium thiosulfate
  2. extractionextracted with ethyl acetate
  3. washwashed with sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of solvent
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-cb4cb256de59461b9b23b85c557a7e85
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415469B2

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