HRID1590729

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID12417418

2-(Bromomethyl)quinoline

C10H8BrN

结构：COC(=O)C(C)(C)Cc1c(C(=O)c2ccc(Cl)cc2)c2ccc(O)cc2n1C

HCID18947581

未命名化合物

PRODUCTS

生成物

结构：COC(=O)C(C)(C)Cc1c(C(=O)c2ccc(Cl)cc2)c2ccc(OCc3ccc4ccccc4n3)cc2n1C

HCID18947635

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

To a solution of 180 mg of the phenol from Step E in 5 mL of DMF were added 124 mg of milled K2CO3 followed by 150 mg of 2-(bromomethyl) quinoline. The mixture was stirred at R.T. for 18 h, poured onto 25% aq. NH4OAc and extracted with ethyl acetate. The extract was dried over Na2SO4 and evaporated to dryness to give an oil which was chromatographed on flash silica gel using ethyl acetate:hexane (30:70) as eluant to give the title compound as a foam.

WORKUP

后处理

extractionextracted with ethyl acetate
dry with materialThe extract was dried over Na2SO4
customevaporated to dryness
customto give an oil which
customwas chromatographed on flash silica gel

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-af7ab0fd95fd45f0801574667aeaaac8
来源数据集: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05204344
来源说明: uspto-grants-1993_04

反应 SMILES

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[C:4]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:3]1[CH2:21][C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24].C([O-])([O-])=O.[K+].[K+].Br[CH2:36][C:37]1[CH:46]=[CH:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:38]=1>CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:36][C:37]3[CH:46]=[CH:45][C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:38]=3)[CH:9]=2)[C:4]([C:12](=[O:20])[C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[C:3]1[CH2:21][C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24]