Triacetoxyperiodinane → 3-(Benzyloxy)-2-methylbenzaldehyde

HRID 253398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 253398
[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 (57, 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 (58, 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-c631cea09bc344879b4b90d66efc94f8
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872018B2

Notizen zur Reaktion

Wird geladen…