Triacetoxyperiodinane → 3-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzoyl]-benzonitrile

HRID 1717743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717743
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:25])[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[CH:12][CH:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(=O)(O)[O-].[Na+]>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[O:25])=[CH:12][CH:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 666995493-{[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzonitrile

Produkt 1

HCID 666995563-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzoyl]-benzonitrileAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Stir a solution of 3-{[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzonitrile (110 mg, 0.264 mmol) in dichloromethane (5 mL) at 0° C. Add Dess-Martin periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (H)-one) (120 mg, 0.29 mmol) and stir the reaction for 1.5 hr at room temperature. Dilute the reaction mixture with aqueous saturated sodium bicarbonate (50 mL) and extract with ethyl acetate (3×50 mL). Dry the combined extracts over sodium sulfate, filter and concentrate. Purify the residue via silica gel chromatography, eluting with 7:3 hexanes:ethyl acetate to afford the title compound as a white solid (105 mg, 95%). Mass spectrum (M+H) 414.

Aufarbeitung

  1. customthe reaction for 1.5 hr at room temperature
  2. extractionextract with ethyl acetate (3×50 mL)
  3. dry with materialDry the combined extracts over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue via silica gel chromatography
  7. washeluting with 7:3 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8e2253b494df441da9029e7b69334363
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803938B2

Notizen zur Reaktion

Wird geladen…