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4-Hydroxybiphenyl → 4-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonitrile

HRID 2266845
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2266845
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][CH2:16][C:17]1[CH:18]=[C:19]([C:23]#[N:24])[O:20][C:21]=1[CH3:22].[C:25]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:25]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:30]=[CH:29][C:28]([O:15][CH2:16][C:17]2[CH:18]=[C:19]([C:23]#[N:24])[O:20][C:21]=2[CH3:22])=[CH:27][CH:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 71034-HydroxybiphenylHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 184446624-Hydroxymethyl-5-methyl-furan-2-carbonitrile

Produkt 1

HCID 184446574-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonitrileAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Diisopropylazodicarboxylate (1.84 g, 10.6 mmoles) was added to a solution of 4-hydroxymethyl-5-methyl-furan-2-carbonitrile (147) (1.32 g, 9.6 mmoles), biphenyl-4-ol (1.63 g, 9.6 mmoles) and triphenylphosphine (4.3 g, 16.35 mmoles) in tetrahydrofuran (50 mL) with stirring and cooling to 0° C. under an argon atmosphere. After 5 minutes, the cooling was removed and the mixture stirred at room temperature for 16 h. The solvent was evaporated and the residue partitioned between ethyl acetate and water. The ethyl acetate phase was washed with brine and dried. After the solvent was evaporated, the residue was purified by flash chromatography (silica, gradient elution with 5% to 10% ethyl acetate in cyclohexane) to afford compound 148 as a white solid (2.2 g). IR (powder) CN st. 2225 cm−1.

Aufarbeitung

  1. customthe cooling was removed
  2. stirringthe mixture stirred at room temperature for 16 h
  3. customThe solvent was evaporated
  4. customthe residue partitioned between ethyl acetate and water
  5. washThe ethyl acetate phase was washed with brine
  6. customdried
  7. customAfter the solvent was evaporated
  8. customthe residue was purified by flash chromatography (silica, gradient elution with 5% to 10% ethyl acetate in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-1bd586cb84c9403a9ef265b3640e8252
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07858644B2

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