Triacetoxyperiodinane → 8-Methyl-1,2,3,4-tetrahydronaphthalene-1-carbaldehyde

HRID 729775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729775
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([CH2:12][OH:13])[CH2:9][CH2:8][CH2:7]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([CH:12]=[O:13])[CH2:9][CH2:8][CH2:7]2

Komponenten

4

Edukt 2

HCID 159087Triacetoxyperiodinane2×HCID 118052711,2,3,4-Tetrahydro-8-methyl-1-naphthalenemethanol

Produkt 1

HCID 220221828-Methyl-1,2,3,4-tetrahydronaphthalene-1-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(8-Methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol (0.03 g, 0.17 mmol) was dissolved in dichloromethane (0.5 mL). To the solution was then added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, also known as Dess-Martin periodinane (0.087 g, 0.20 mmol). The reaction mixture was stirred for 2 hrs then partitioned with an aqueous saturated solution of thiosulfate and dichloromethane. The organic layer was washed with an aqueous saturated solution of thiosulfate, an aqueous saturated solution of sodium bicarbonate, brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield 8-methyl-1,2,3,4-tetrahydro-naphthalene-1-carbaldehyde as a solid.

Aufarbeitung

  1. customthen partitioned with an aqueous saturated solution of thiosulfate and dichloromethane
  2. washThe organic layer was washed with an aqueous saturated solution of thiosulfate
  3. dry with materialan aqueous saturated solution of sodium bicarbonate, brine, dried with Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2b79daddb727469c827a713f4c0d5b96
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582649B2

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