HRID442815

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID82712

4-Hydroxy-3,5-bis(isopropyl)benzaldehyde

C13H18O2

HCID142163

Sulphonyl diacetonitrile

C4H4N2O2S

PRODUCTS

生成物

$结构：CC(C)c1cc(/C=C(\C#N)S(=O)(=O)CC#N)cc(C(C)C)c1O$

HCID9905645

未命名化合物

$结构：CC(C)c1cc(/C=C(\C#N)S(=O)(=O)/C(C#N)=C/c2cc(C(C)C)c(O)c(C(C)C)c2)cc(C(C)C)c1O$

HCID10186353

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID8082

Piperidine

C5H11N

溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

A mixture of 500 mg of 3,5-diisopropyl-4-hydroxybenzaldehyde and 700 mg of sulphonyl diacetonitrile in 6 ml of ethanol was refluxed with a few drops of piperidine for 4 hours. Ethanol was removed in a rotavap and the mixture worked up with ethyl acetate, diluted acid and brine. A portion of the crude was then purified by HPLC on a C-18 column to provide 50 mg of the titled compound along with 30 mg of (E,E)-2-[[1--Cyano-2-(3,5-diisopropyl-4-hydroxyphenyl)ethenyl]sulfonyl]-3-(3,5-diisopropyl-4-hydroxyphenyl)acrylonitrile.

WORKUP

后处理

customEthanol was removed in a rotavap
additiondiluted acid and brine
customA portion of the crude was then purified by HPLC on a C-18 column

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-176c1636fb854f6b8b17c03e7c09027c
来源数据集: uspto-grants-1999_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05891917
来源说明: uspto-grants-1999_04

反应 SMILES

[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])[CH:7]=O)([CH3:3])[CH3:2].[S:16]([CH2:22][C:23]#[N:24])([CH2:19][C:20]#[N:21])(=[O:18])=[O:17]>C(O)C.N1CCCCC1>[C:20]([CH2:19][S:16](/[C:22](=[CH:7]/[C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:11]([OH:12])=[C:10]([CH:13]([CH3:15])[CH3:14])[CH:9]=1)/[C:23]#[N:24])(=[O:18])=[O:17])#[N:21].[C:20](/[C:19](/[S:16](/[C:22](=[CH:7]/[C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:11]([OH:12])=[C:10]([CH:13]([CH3:15])[CH3:14])[CH:9]=1)/[C:23]#[N:24])(=[O:18])=[O:17])=[CH:7]\[C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:11]([OH:12])=[C:10]([CH:13]([CH3:15])[CH3:14])[CH:9]=1)#[N:21]