Dichloromethane → 3-(4-Triisopropylsilanyloxymethyl-benzoyl)-benzonitrile

HRID 1717765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717765
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[CH:13][CH:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.ClCCl>C(=O)([O-])O.[Na+]>[CH:26]([Si:19]([CH:20]([CH3:22])[CH3:21])([CH:23]([CH3:25])[CH3:24])[O:18][CH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:2]([C:3]2[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=2)[C:6]#[N:7])=[O:1])=[CH:16][CH:15]=1)([CH3:28])[CH3:27]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 666996123-[Hydroxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile

Produkt 1

HCID 574383603-(4-Triisopropylsilanyloxymethyl-benzoyl)-benzonitrileAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of 3-[hydroxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile (2.06 g, 5.21 mmol), Dess-Martin periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(H)-one) (2.7 g, 6.25 mmol), and dichloromethane (50 mL) is stirred at room temperature 24 hr. The mixture is diluted with aqueous saturated sodium hydrogen carbonate and extracted with dichloromethane (2×50 ml). The combined extracts are dried over magnesium sulfate, filtered, and concentrated. The residue is purified via silica chromatography eluting with hexanes to 8:2 hexanes:ethyl acetate to give the title compound (1.2 g, 60%) as a white solid. 1H NMR (CDCl3) δ 8.06-8.10 (m, 2H), 7.89-7.91 (m, 1H), 7.79-7.81 (m, 2H), 7.66 (t, 1H), 7.54-7.56 (m, 2H), 4.97 (s, 2H), 1.17-1.31 (m, 21H).

Aufarbeitung

  1. extractionextracted with dichloromethane (2×50 ml)
  2. dry with materialThe combined extracts are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified via silica chromatography
  6. washeluting with hexanes to 8:2 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-cb89d251a11d4cbabb2a8ee4f5021af9
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803938B2

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