Dimethylformamide → 4-(Hydroxymethyl)thiophene-2-carbonitrile

HRID 619833

Reaktionsgleichung

Reaktionsgleichung von HRID 619833
I[C:2]1[S:6][CH:5]=[C:4]([CH2:7][OH:8])[CH:3]=1.[CH3:9][N:10](C=O)C>CCOC(C)=O.[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:8][CH2:7][C:4]1[CH:3]=[C:2]([C:9]#[N:10])[S:6][CH:5]=1

Komponenten

6

Edukt 2

HCID 6228DimethylformamideHCID 22559990(5-Iodothiophen-3-yl)methanol

Produkt 1

HCID 106542884-(Hydroxymethyl)thiophene-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of (5-iodothiophene-3-yl)methanol (42 g, 176 mmol) in 150 mL of DMF is added Zn(CN)2 (12.4 g, 106 mmol) and Pd(PPh3)4 (8.13 g, 7.04 mmol). The solution is heated to 80° C. After 6 hours, the solution is diluted with 3 L of EtOAc. The resulting solution is washed with 1 N NH4OH, H2O and sat. NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes to afford the title compound (10 g, 72 mmol) as a clear oil.

Aufarbeitung

  1. washThe resulting solution is washed with 1 N NH4OH, H2O and sat. NaCl
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography
  6. washeluting with gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bd47b668258a41c0903fc816ad49a343
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958918

Verknüpfte Notizen

Wird geladen…