Dimethylformamide → 2-(Hydroxymethyl)-2,3-dihydro-1H-indene-5-carbonitrile

HRID 1466039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1466039
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([CH2:11][OH:12])[CH2:5]2.[CH3:13][N:14](C=O)C>[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:12][CH2:11][CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:13]#[N:14])[CH:3]=2)[CH2:7]1

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 68507961(5-Bromo-2,3-dihydro-1H-inden-2-yl)methanol

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of (5-Bromo-2,3-dihydro-1H-inden-2-yl)methanol (10 g, 44 mmol), Zn(CN)2 (10.3 g, 88 mmol) and Pd(PPh3)4 (1 g, 0.88 mmol) in 100 mL of DMF was heated at 100-120° C. under N2 atmosphere overnight. Most of the solvent was concentrated and the residue was partitioned between water (100 mL) and EtOAc (100 mL) and separated. The aqueous layer was extracted with EtOAc (50 mL×2). The combined organic layers were washed with brine (200 mL), dried over Na2SO4 and concentrated to dryness. The residue was purified with column chromatography (EtOAc/PE=1:20) to give the title compound. 1H-NMR (400 MHz, CDCl3) δ 7.45 (s, 1H), 7.41 (d, J=7.6 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 3.64 (d, J=6.6 Hz, 2H), 3.05-3.13 (m, 2H), 2.70-2.84 (m, 3H).

Aufarbeitung

  1. concentrationMost of the solvent was concentrated
  2. customthe residue was partitioned between water (100 mL) and EtOAc (100 mL)
  3. customseparated
  4. extractionThe aqueous layer was extracted with EtOAc (50 mL×2)
  5. washThe combined organic layers were washed with brine (200 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe residue was purified with column chromatography (EtOAc/PE=1:20)

Quellen und Nachweise

ORD-Eintrag
ord-badcbf6fedf94e698f285b18c23b2583
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999990B2

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