Triacetoxyperiodinane → 1-formyl-3,4-dihydro-1H-isochromene-5-carbonitrile

HRID 1187027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1187027
[OH:1][CH2:2][CH:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:13]#[N:14])[C:7]=2[CH2:6][CH2:5][O:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([CH:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:13]#[N:14])[C:7]=2[CH2:6][CH2:5][O:4]1)=[O:1]

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 666465561-(hydroxymethyl)-3,4-dihydro-1H-isochromene-5-carbonitrile

Produkt 1

HCID 595686551-formyl-3,4-dihydro-1H-isochromene-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1-(hydroxymethyl)-3,4-dihydro-1H-isochromene-5-carbonitrile (0.16 g, 0.85 mmol) in 4 mL of DCM was added Dess-Martin reagent (0.72 g, 1.7 mmol) in one portion at 0° C. The mixture was stirred at 0° C. for 1 hour, and then stirred at rt. overnight. The reaction mixture was filtered and the filtrate was concentrated to give 1-formyl-3,4-dihydro-1H-isochromene-5-carbonitrile. 1H-NMR (400 MHz, CDCl3) δ 9.71 (s, 1H), 7.93˜7.95 (m, 1H), 7.64˜7.68 (m, 1H), 4.99 (s, 1H), 4.03˜4.09 (m, 2H), 2.99˜3.04 (m, 2H).

Aufarbeitung

  1. stirringstirred at rt
  2. customovernight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-53192104c8f24379b6592453d66c3200
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673920B2

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