N,N,N',N'-Tetramethylethylenediamine → 4-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile

HRID 2173256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173256
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH:7]2[CH2:12][OH:13].[CH3:14][N:15](CCN(C)C)C.CCOC(C)=O>CN(C=O)C.[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:13][CH2:12][CH:7]1[C:6]2[C:11](=[C:2]([C:14]#[N:15])[CH:3]=[CH:4][CH:5]=2)[O:10][CH2:9][CH2:8]1

Komponenten

7

Edukt 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8857Ethyl AcetateHCID 67516017(8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol

Produkt 1

HCID 675169644-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of (8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol (1 g, 4.12 mmol) in 3 mL of DMF was added Zn(CN)2 (481 mg, 4.12 mmol), Pd2(dba)3 (67 mg, 0.04 mmol), TMEDA (191 mg, 1.6 mmol), Xantphose (48 mg, 0.08 mmol), and the mixture was stirred under microwave irradiation for 5 min at 100° C. The mixture was added with 10 mL of EtOAc, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give 4-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile.

Aufarbeitung

  1. washwashed with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-TLC

Quellen und Nachweise

ORD-Eintrag
ord-74a2ab077706474a9f188b275b8fb0f3
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056859B2

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