HRID660643

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID12192

Ethyl diazoacetate

C4H6N2O2

结构：C=Cc1ccc(N2CC(=O)N(CC[Si](C)(C)C)S2(=O)=O)c(OCc2ccccc2)c1

HCID66756542

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)C1CC1c1ccc(N2CC(=O)N(CC[Si](C)(C)C)S2(=O)=O)c(OCc2ccccc2)c1

HCID68839918

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Rh+2].[Rh+2]

催化剂HCID152122

未命名化合物

溶剂HCID6344

Dichloromethane

CH2Cl2

2 次

PROCEDURE

实验过程

To a solution of 5-(2-benzyloxy-4-vinylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (Example 81, step A) (75 mg, 0.17 mmol) in methylene chloride is added rhodium acetate dimer (cat.). Ethyl diazoacetate (0.024 mL, 0.17 mmol) in methylene chloride (0.2 mL) is added dropwise via syringe pump over 4 h. The solvent is removed under reduced pressure and the crude material purified on silica gel using a gradient of 0-40% EtOAc/hexanes to give the title compound as a mixture of isomers (cis:trans 1:2) as a colorless oil: (M+H)+=548.

WORKUP

后处理

customThe solvent is removed under reduced pressure
customthe crude material purified on silica gel using a gradient of 0-40% EtOAc/hexanes

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8c40f294a41e4289aaae9ead84183b7b
来源数据集: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08084448B2
来源说明: uspto-grants-2011_12

反应 SMILES

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[CH:12]=[CH:11][C:10]=1[N:17]1[S:21](=[O:23])(=[O:22])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:19](=[O:30])[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[N-]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[CH2:37]([O:36][C:34]([CH:33]1[CH2:16][CH:15]1[C:13]1[CH:12]=[CH:11][C:10]([N:17]2[CH2:18][C:19](=[O:30])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[S:21]2(=[O:23])=[O:22])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1)=[O:35])[CH3:38]