Triphenylphosphine → HCID 178445771, Verbindung

HRID 2404136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2404136
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]#[N:13])[CH:6]=[CH:5]2.[C:14]([C@@H:18]1[CH2:23][CH2:22][C@H:21](O)[CH2:20][CH2:19]1)([CH3:17])([CH3:16])[CH3:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O.C1(C)C=CC=CC=1>[C:14]([C@H:18]1[CH2:23][CH2:22][C@H:21]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C:12]#[N:13])[CH:6]=[CH:5]3)[CH2:20][CH2:19]1)([CH3:17])([CH3:16])[CH3:15]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 45894766-Hydroxy-2-naphthonitrileHCID 5363146Diisopropyl azodicarboxylateHCID 178445811HCID 178445811, Verbindung

Produkt 1

HCID 178445771HCID 178445771, VerbindungAusbeute 146,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a vial charged with 6-hydroxy-2-naphthonitrile (3.38 g, 0.02 mol, 1.0 eq.), cis-4-tert-butylcyclohexanol (6.24 g, 0.04 mol, 2.0 eq.), PPh3 (10.5 g, 0.04 mol, 2.0 eq.) and toluene (20 mL), was added DIAD (12 mL, 0.06 mol, 3.0 eq.) under nitrogen atmosphere at r.t. and stirred for 15 h. Water was added and extracted with EtOAc. The organic layer was purified by silica gel chromatography (PE:EA=10:1) to give the title compound (9.0 g, 86%) as a slight yellow solid. EDI-MS (M+1)+: 308.0. 1H NMR (400 MHz, CDCl3) δ 8.12 (s, 1H), 7.78-7.73 (m, 2H), 7.54 (dd, 1H), 7.22 (dd, 1H), 7.14 (s, 1H), 4.33-4.30 (m, 1H), 2.29-2.25 (m, 2H), 1.93-1.90 (m, 2H), 1.48-1.26 (m, 2H), 1.25-1.10 (m, 3H), 0.91 (s, 9H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic layer was purified by silica gel chromatography (PE:EA=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-c00fd199fa7d4b64b461b7feb25514ea
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802659B2

Notizen zur Reaktion

Wird geladen…