二氯甲烷 → Didodecyl 2-(thiophen-3-yl)malonate

HRID 335353笔记

反应方程式

HRID 335353 反应方程式
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([C:10]([OH:12])=[O:11])[C:7]([OH:9])=[O:8])=[CH:2]1.[CH2:13](O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CS(O)(=O)=O.C(Cl)Cl>C1COCC1>[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([C:7]([O:9][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])=[O:8])[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:11])=[CH:2]1

参与物

6

反应物 4

HCID 6344二氯甲烷HCID 6395甲基磺酸HCID 8193十二醇HCID 887823-噻吩丙二酸

产物 1

HCID 70983275Didodecyl 2-(thiophen-3-yl)malonate收率 69%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

In a one-necked flask, 3-thienylmalonic acid (10.0 g, 53.7 mmol) and 1-dodecanol (4 eq., 40.0 g, 215 mmol) were dissolved in THF (80 mL) at room temperature. To this solution was added methanesulphonic acid (1.99 g, 20.7 mmol). The reaction mixture was stirred at room temperature for 3 days. The solvent was then evaporated at 40° C. The residue was re-dissolved in CH2Cl2 to form a solution, which was loaded onto a column (eluent: CH2Cl2) to give didodecyl 2-(thiophen-3-yl)malonate (yield: 18.0 g, 69%). 1H NMR (CDCl3): 0.9 (6H, t), 1.3 (36H, m), 1.7 (4H, m), 4.2 (4H, t), 4.8 (1H, s), 7.2 (1H, d), 7.3 (1H, d), 7.4 (1H, s).

后处理

  1. customThe solvent was then evaporated at 40° C
  2. dissolutionThe residue was re-dissolved in CH2Cl2
  3. customto form a solution, which

来源与证据

ORD记录
ord-c14abc847f884fe880e957398e1c90c8
来源数据集
uspto-grants-2014_11
专利号
US08883954B2

反应笔记

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