1-Cyclohexenylboronic acid → 4-(1-Cyclohexen-1-yl)-3-ethylbenzonitrile

HRID 423307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423307
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1I)[C:6]#[N:7])[CH3:2].[C:12]1(B(O)O)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1.C[O-].[Na+]>CO.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:12]1([C:10]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[CH2:1][CH3:2])[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1

Komponenten

6

Edukt 3

HCID 38629021-Cyclohexenylboronic acidHCID 10942334Sodium MethoxideHCID 593167183-Ethyl-4-iodobenzonitrile

Produkt 1

HCID 593167164-(1-Cyclohexen-1-yl)-3-ethylbenzonitrileAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-ethyl-4-iodobenzonitrile (D16) (1.23 g, 4.80 mmol), 1-cyclohexen-1-ylboronic acid (907 mg, 7.20 mmol), sodium methoxide (778 mg, 14.4 mmol) and bis(triphenylphosphine)palladium (II) chloride (337 mg, 0.48 mmol) in anhydrous methanol (12 mL) was heated at 80° C. for 10 minutes in the microwave. The reaction mixture was partitioned between ethyl acetate (40 mL) and water (40 mL) before the organic layer was further washed with water (40 mL), dried (phase separator) and concentrated in vacuo. The crude material was purified by silica chromatography, eluting 0-5% EtOAc in hexane over 30 minutes to give the title compound as a yellow oil (824 mg, 3.91 mmol). δH (methanol-d4, 400 MHz) 7.56 (1H, d), 7.46 (1H, dd), 7.19 (1H, d), 5.61-5.56 (1H, m), 2.68 (2H, quart), 2.23-2.16 (4H, m), 1.85-1.68 (4H, m), 1.20 (3H, t). MS (ES): No mass ion observed.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate (40 mL) and water (40 mL) before the organic layer
  2. washwas further washed with water (40 mL)
  3. customdried (phase separator)
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica chromatography
  6. washeluting 0-5% EtOAc in hexane over 30 minutes

Quellen und Nachweise

ORD-Eintrag
ord-1d9f5b25ad2a400f87a38c8917aa6a69
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101775B2

Notizen zur Reaktion

Wird geladen…