Triacetoxyperiodinane → 2-Formyl-2,3-dihydro-1H-indene-5-carbonitrile

HRID 1466040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1466040
[OH:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]#[N:13])[CH:9]=2)[CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]#[N:13])[CH:9]=2)[CH2:4]1)=[O:1]

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 685123302-(Hydroxymethyl)-2,3-dihydro-1H-indene-5-carbonitrile

Produkt 1

HCID 724441512-Formyl-2,3-dihydro-1H-indene-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2-(Hydroxymethyl)-2,3-dihydro-1H-indene-5-carbonitrile (3.7 g, 21 mmol) in 80 mL of DCM was added Dess-Martin reagent (18 g, 43 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 purified with column chromatography (EtOAc:PE=1:20) to obtain 2-Formyl-2,3-dihydro-1H-indene-5-carbonitrile. 1H-NMR (400 MHz, CDCl3) δ 9.77 (d, J=1.2 Hz, 1H), 7.45-7.51 (m, 2H), 7.32 (d, J=7.6 Hz, 1H), 3.32-3.40 (m, 3H), 3.18-3.25 (m, 2H).

Aufarbeitung

  1. stirringstirred at rt
  2. customovernight
  3. customThe reaction mixture was purified with column chromatography (EtOAc:PE=1:20)

Quellen und Nachweise

ORD-Eintrag
ord-870b834cc1304e269cb377a5c8b5d91e
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999990B2

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