反応式
C(O)(=O)C.C[Si](N[Si](C)(C)C)(C)C.[I:14][C:15]1[S:19][C:18]([C:20](=O)[CH3:21])=[CH:17][C:16]=1[CH3:23].[C:24]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])#[N:25]>CCOC(C)=O>[CH2:30]([O:29][C:27](=[O:28])[C:26]([C:24]#[N:25])=[C:20]([C:18]1[S:19][C:15]([I:14])=[C:16]([CH3:23])[CH:17]=1)[CH3:21])[CH3:31]参加物
反応条件
- 温度
- 80 °C
実験手順
Acetic acid (9.4 ml) was placed in a flask at rt and HMDS (3.0 ml, 14.1 mmol) was added dropwise. After the exotherm subsided, 1-(5-Iodo-4-methyl-thiophen-2-yl)-ethanone (2.5 g, 9.4 mmol) was added as a solid followed by ethyl cyanoacetate (2.0 ml, 18.8 mmol). The reaction was stirred at 80° C. for 8 h, cooled to rt and concentrated by rotary evaporation to give a brown residue. The residue was taken up in EtOAc, washed with NaHCO3 (aq, sat.) and then with H2O. The organics were dried (NaSO4), filtered and concentrated to give a brown solid. The solid was triturated with EtOH and filtered to give 2-Cyano-3-(5-iodo-4-methyl-thiophen-2-yl)-but-2-enoic acid ethyl ester (2.0 g, 5.5 mmol, 58%) as a light yellow solid. MS (ESI) m/z 362.0 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ ppm 1.27 (t, 1H) 2.21 (s, 1H) 2.66 (s, 1H) 4.26 (q, 1H) 7.67 (s, 4H).
後処理
- temperaturecooled to rt
- concentrationconcentrated by rotary evaporation
- customto give a brown residue
- washwashed with NaHCO3 (aq, sat.)
- dry with materialThe organics were dried (NaSO4)
- filtrationfiltered
- concentrationconcentrated
- customto give a brown solid
- customThe solid was triturated with EtOH
- filtrationfiltered
出典と根拠
- ORDレコード
- ord-37533cd780f941d3905b4fbf8deee233
- 出典データセット
- uspto-grants-2006_10
- 特許番号
- US07119205B2
関連ノート
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