Triacetoxyperiodinane → [6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-acetaldehyde

HRID 2404204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2404204
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:22][CH2:23][OH:24])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:22][CH:23]=[O:24])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 669266452-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-ethanol

Produkt 1

HCID 86668430[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-acetaldehydeAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2-[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-ethanol (170 mg, 0.52 mmol) in methylene chloride (5 mL) was added Dess-Martin periodinane (0.31 g, 0.73 mmol). After stirred at room temperature for 1 hour, the solution was diluted with methylene chloride, washed with sodium thiosulfate aqueous, dried over Na2SO4, and concentrated. The crude was purified via silica gel column to afford white solid (120 mg, yield: 70%). ESI-MS: 325.20 (M+H)+.

Aufarbeitung

  1. washwashed with sodium thiosulfate aqueous
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude was purified via silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-301cefb46edb4805b73015aafabb18a4
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802659B2

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