HCID 67315923、化合物 → Ethyl β-methyl-2-naphthalenepropanoate

HRID 1014766ノート

反応式

HRID 1014766 の反応式
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH3:18])=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>[Ir].C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([CH3:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

参加物

4

反応物 1

HCID 67315923HCID 67315923、化合物

生成物 1

HCID 57055028Ethyl β-methyl-2-naphthalenepropanoate収率 99%

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-(naphthalen-2-yl)-but-2-enoate) (70 mg, 0.29 mmol) and iridium catalyst (S)-32 (9.2 mg, 0.0058 mmol, 2.0 mol %) in CH2Cl2 (3 mL) was hydrogenated. Removal of the solvent in vacuo and standard purification gave 38 (70 mg, 99%) as a colorless oil. [α]20D −25.9 (c 1.02, CHCl3); CSP HPLC analysis (Chiralcel OD-H; eluent: 99.5:0.5 hexanes/i-PrOH, 1.0 ml/min) determined a 89.5:10.5 er (79% ee) [tR(minor) 12.34 min, tR(major) 14.19 min]; 1H NMR (300 MHz, CDCl3) 7.82 (d, 3H, J=8.4 Hz), 7.69 (s, 1H), 7.51-7.39 (m, 3H), 4.11 (q, 2H, J=7.2 Hz), 3.50 (sextet, 1H, J=7.5 Hz), 2.81-2.62 (m, 2H), 1.42 (d, 3H, J=6.9 Hz), 1.19 (t, 3H, J=7.2 Hz) ppm; 13C NMR (75 MHz, CDCl3) 172.3, 143.1, 135.5, 132.3, 128.1, 127.6, 127.5, 125.9, 125.4, 125.3, 124.9, 60.2, 42.8, 42.6, 36.6, 21.7, 14.1 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-534bff48ce4742908e4a2ad9a75fa60d
出典データセット
uspto-grants-2011_07
特許番号
US07982064B2

反応ノート

読み込み中…