Dichloromethane → 1,2-Diphenylpropane

HRID 1014761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1014761
C[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:16](Cl)Cl>[Ir]>[C:10]1([CH2:9][CH:8]([C:3]2[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH3:16])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

4

Edukt 2

HCID 6344DichloromethaneHCID 6066552-Methylstilbene

Produkt 1

HCID 220681,2-DiphenylpropaneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23924IridiumKatalysator

Versuchsvorschrift

According to the general procedure, a solution of methyl stilbene (57 mg, 0.29 mmol) and iridium catalyst (S)-32 (9.4 mg, 0.0060 mmol, 2.0 mol %) in CH2Cl2 (3 mL) was hydrogenated. Removal of the solvent in vacuo and standard purification gave 33 (54 mg, 94%) as a colorless oil; [α]20D −55.2 (c 1.00, CHCl3); Chiral GC analysis (Chirasil DEX-CB; program: 100° C. for 5 min, the 0.5° C./min to 140° C. for 5 min, then 2° C./min to 180° C. for 10 min) determined a 86:14 er (72% ee) [tR(minor) 66.26 min, tR(major) 66.66 min]; 1H NMR (300 MHz, CDCl3) 7.37-7.30 (m, 3H), 7.24-7.20 (m, 2H), 7.14 (d, 2H, J=7.2 Hz), 3.13-2.98 (m, 2H), 2.82 (q, 1H, J=7.8 Hz), 1.31 (d, 3H, J=6.6 Hz) ppm; 13C NMR (75 MHz, CDCl3) 147.0, 140.8, 129.1, 128.3, 128.1, 127.0, 126.0, 125.8, 45.0, 41.8, 21.1 ppm.

Aufarbeitung

  1. customRemoval of the solvent
  2. customin vacuo and standard purification

Quellen und Nachweise

ORD-Eintrag
ord-005c4c8c6d374f6e82d0bac420c9ef79
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07982064B2

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