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

HRID 713983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 713983
[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-f3075bd42dc5431f8fb5045f7e438c2a
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09186367B2

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