Cornforth reagent → Spiro(2.5)octane-6-carbaldehyde

HRID 15289

Reaktionsgleichung

Reaktionsgleichung von HRID 15289
[CH2:1]1[C:3]2([CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][CH2:4]2)[CH2:2]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:2]1[C:3]2([CH2:8][CH2:7][CH:6]([CH:9]=[O:10])[CH2:5][CH2:4]2)[CH2:1]1

Komponenten

4

Edukt 2

HCID 2724130Cornforth reagentHCID 53487089(Spiro(2.5)octan-6-yl)methanol

Produkt 1

HCID 86598198Spiro(2.5)octane-6-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Spiro[2.5]oct-6-yl-methanol (2.57 g, 18.3 mmol, 1.0 eq.) was dissolved in CH2Cl2 (30 mL) and placed in a ice-water bath at 0° C. Pyridinium dichromate (PCC) (7.9 g, 36.6 mmol, 2.0 eq.) was added and the reaction warmed to room temperature for 4 hours with stirring. The crude reaction was filtered through a Celite pad and washed with CH2Cl2 and evaporated. The crude material was dissolved in diethyl ether and filtered through Celite, washing with diethyl ether several times. Evaporated solvent to provide Spiro[2.5]octane-6-carbaldehyde as a brown oil (2.98 g, quantitative) that was used directly. 1H NMR (CHCl3, 400 MHz) δ 0.17-0.27 (m, 4H), 0.88-0.91 (m, 2H), 1.09-1.25 (m, 2H), 1.52-1.54 (m, 2H), 1.69-1.75 (m, 3H), 9.44 (d, 1H, J=1.2 Hz).

Aufarbeitung

  1. customplaced in a ice-water bath at 0° C
  2. customThe crude reaction
  3. filtrationwas filtered through a Celite pad
  4. washwashed with CH2Cl2
  5. customevaporated
  6. dissolutionThe crude material was dissolved in diethyl ether
  7. filtrationfiltered through Celite
  8. washwashing with diethyl ether several times

Quellen und Nachweise

ORD-Eintrag
ord-c30f4ecb7f5a47108df6f7c307355618
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732449B2

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