Ethyl 3-(4-methoxyphenyl)-2-methylprop-2-enoate → Ethyl 3-(4-methoxyphenyl)-2-methylpropanoate

HRID 1014765ノート

反応式

HRID 1014765 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1>[Ir].C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:8]=1

参加物

4

反応物 1

HCID 53711494Ethyl 3-(4-methoxyphenyl)-2-methylprop-2-enoate

生成物 1

HCID 11160380Ethyl 3-(4-methoxyphenyl)-2-methylpropanoate収率 96.4%

試薬・触媒・溶媒 2

HCID 23924Iridium触媒HCID 6344Dichloromethane溶媒

実験手順

According to the general procedure, a solution of ethyl 3-(4-methoxyphenyl)-2-methylacrylate (30 mg, 0.14 mmol) and iridium catalyst (S)-32 (4.5 mg, 0.0029 mmol, 2.0 mol %) in CH2Cl2 (1.4 mL) was hydrogenated. Removal of the solvent in vacuo and standard purification gave 37 (30 mg, 96%) as a colorless oil. [α]20D +24.5 (c 1.25, CHCl3); CSP HPLC analysis (Chiralcel OB-H; eluent: 99.5:0.5 hexanes/i-PrOH, 0.5 mL/min) determined a 90:10 er (80% ee) [tR(minor) 9.01 min, tR(major) 9.76 min]; 1H NMR (300 MHz, CDCl3) 7.08 (d, 2H, J=8.7 Hz), 6.81 (d, 2H, J=8.7 Hz), 4.09 (q, 2H, J=7.2 Hz), 3.78 (s, 3H), 3.01-2.90 (m 1H), 2.73-2.57 (m, 2H), 1.19 (t, 3H, J=7.2 Hz), 1.13 (d, 3H, J=6.6 Hz) ppm; 13C NMR (75 MHz, CDCl3) 176.2, 158.1, 131.4, 129.9, 113.7, 60.2, 55.2, 41.7, 38.8, 16.7, 14.2 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-8d8eec3572974c5fa9d3a31da4db50e6
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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