碳酸钾 → Ethyl 3-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylate

HRID 215744

反应方程式

HRID 215744 反应方程式
Cl[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[C:8]#[N:9].C([O-])([O-])=O.[K+].[K+].[CH2:16]([O:18][C:19](=[O:22])[CH2:20][SH:21])[CH3:17]>CCO.C1COCC1>[CH2:16]([O:18][C:19]([C:20]1[S:21][C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[C:8]=1[NH2:9])=[O:22])[CH3:17]

参与物

5

反应物 3

HCID 11430碳酸钾HCID 12185巯基乙酸乙酯HCID 498409392-氯环己-1-烯-1-腈

产物 1

HCID 312340Ethyl 3-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylate收率 101.4%

试剂、催化剂与溶剂 1

HCID 21873804Tetrahydrofuran ethanol溶剂

反应条件

温度
90 °C

实验过程

A 250 mL flask was charged with 2-chloro-cyclohex-1-enecarbonitrile (3.0 g, 21 mmol) in a 6:1 mixture of EtOH/THF (42 mL), K2CO3 (2.9 g, 21 mmol), and mercapto-acetic acid ethyl ester (3.5 mL, 32 mmol), after which it was fitted with a reflux condenser under N2 atmosphere and heated to 90° C. for 24 h. The mixture was filtered through a pad of diatomaceous earth, such as Celite®, rinsing thoroughly with MeOH (400 mL). After concentration, the title compound was purified by FCC (60% ethyl acetate (EtOAc)/hexanes) to give an amber-colored oil (4.8 g). MS: 226.1. 1H NMR (400 MHz, CDCl3) δ ppm 5.35 (s, 2H), 2.71-2.64 (m, 2H), 2.36-2.26 (m, 2H), 1.87-1.77 (m, 4H), 1.33 (t, J=7.1 Hz, 3H).

后处理

  1. customafter which it was fitted with a reflux condenser under N2 atmosphere
  2. filtrationThe mixture was filtered through a pad of diatomaceous earth, such as Celite®
  3. washrinsing thoroughly with MeOH (400 mL)
  4. concentrationAfter concentration
  5. customthe title compound was purified by FCC (60% ethyl acetate (EtOAc)/hexanes)

来源与证据

ORD记录
ord-c33d6f2090744fc383edb9addea09a90
来源数据集
uspto-grants-2012_06
专利号
US08193178B2

关联笔记

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