Dichloromethane → 1,2-Diphenylpropane

HRID 1014761Notes

Reaction equation

HRID 1014761 reaction equation
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

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 6066552-Methylstilbene

Product 1

HCID 220681,2-DiphenylpropaneYield 94%

Reagents, catalysts & solvents 1

HCID 23924IridiumCatalyst

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-005c4c8c6d374f6e82d0bac420c9ef79
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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