Dichloromethane → 1,2-Diphenylpropane

HRID 1014761ノート

反応式

HRID 1014761 の反応式
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

参加物

4

反応物 2

HCID 6344DichloromethaneHCID 6066552-Methylstilbene

生成物 1

HCID 220681,2-Diphenylpropane収率 94%

試薬・触媒・溶媒 1

HCID 23924Iridium触媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-005c4c8c6d374f6e82d0bac420c9ef79
出典データセット
uspto-grants-2011_07
特許番号
US07982064B2

反応ノート

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