HRID987233

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID887

Methanol

CH4O

HCID3939

Lithium hydroxide anhydrous

HLiO

结构：CCOC(=O)C(C#N)=Cc1ccc(OCCc2ccc(OS(C)(=O)=O)cc2)cc1

HCID86595057

未命名化合物

PRODUCTS

生成物

结构：N#CC(=Cc1ccc(OCCc2ccc(O)cc2)cc1)C(=O)O

HCID69629265

未命名化合物

结构：CS(=O)(=O)Oc1ccc(CCOc2ccc(C=C(C#N)C(=O)O)cc2)cc1

HCID86595058

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

2 次

PROCEDURE

实验过程

2-Cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}acrylic acid ethyl ester (described in Example 6) (0.201 g; 0.483 mmole), lithium hydroxide (0.04 g; 1.67 mmole), methanol (2.3 ml) and water (2.3 ml) was stirred at 40° C. for 23 hours. More water was added, methanol was removed by evaporation in vacuo and the mixture was acidified using potassium hydrogen sulfate. The mixture was extracted with ethyl acetate and the organic phase was dried (sodium sulfate), filtered and evaporated in vacuo. The crude products were purified on preparative HPLC using acetonitrile (gradient 30-60%): ammonium acetate (0.1 M). The fractions were acidified with potassium hydrogen sulfate and then extracted with ethyl acetate. The organic phases were combined and evaporated in vacuo to give 7 mg of 2-cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]-phenyl}acrylic acid and 21,8 mg of 2-cyano-3-{4-[2-(4-hydroxyphenyl)ethoxy]phenyl}-acrylic acid.

WORKUP

后处理

custommethanol was removed by evaporation in vacuo
extractionThe mixture was extracted with ethyl acetate
dry with materialthe organic phase was dried (sodium sulfate)
filtrationfiltered
customevaporated in vacuo
customThe crude products were purified on preparative HPLC
extractionextracted with ethyl acetate
customevaporated in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-0b325fc0d41f45b39f6d5adff9c37d64
来源数据集: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06630600B1
来源说明: uspto-grants-2003_10

反应 SMILES

C([O:3][C:4](=[O:29])[C:5]([C:27]#[N:28])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)C.[OH-].[Li+].CO>O>[C:27]([C:5](=[CH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:11][CH:12]=1)[C:4]([OH:29])=[O:3])#[N:28].[C:27]([C:5](=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)[C:4]([OH:29])=[O:3])#[N:28]