HRID1898717

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

结构：O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[Ce+4].[NH4+].[NH4+]

HCID180504

未命名化合物

HCID516892

Sodium Bicarbonate

CHNaO3

结构：Cc1c(C)c2c(c(C)c1O)CCC(C)(C(=O)NCc1ccccn1)O2

HCID21737544

未命名化合物

PRODUCTS

生成物

结构：CC1=C(C)C(=O)C(CCC(C)(O)C(=O)NCc2ccccn2)=C(C)C1=O

HCID42599389

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

溶剂HCID69430

2-Oxopropiononitrile

C3H3NO

PROCEDURE

实验过程

A solution of 6-hydroxy-2,5,7,8-tetramethyl-N-(pyridin-2-ylmethyl)chroman-2-carboxamide (104 mg, 0.307 mmol) in 4 mL AcCN was chilled to 0° C. and CAN (370 mg in 2 mL H2O) added followed by 8 mL EtOAc, 4 mL 1.0 M NaHCO3 and 250 mg K2CO3. The emulsion was extracted 5×4 mL EtOAc and the combined organics washed 2×4 mL saturated NaCl, dried over Na2SO4 and concentrated to yellow oil. Flash chromatography yielded 2-hydroxy-2-methyl-N-(pyridin-2-ylmethyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide.

WORKUP

后处理

extractionThe emulsion was extracted 5×4 mL EtOAc
washthe combined organics washed 2×4 mL saturated NaCl
dry with materialdried over Na2SO4
concentrationconcentrated to yellow oil

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-edecc1a2f6b444b7b7deca8839f685a2
来源数据集: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08519001B2
来源说明: uspto-grants-2013_08

反应 SMILES

[OH:1][C:2]1[C:3]([CH3:25])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:24])([C:14]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[O:15])[CH2:6][CH2:5]2.[O:26]=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C([O-])(O)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C(C#N)(C)=O.CCOC(C)=O>[OH:26][C:7]([CH3:24])([CH2:6][CH2:5][C:4]1[C:9](=[O:8])[C:10]([CH3:13])=[C:11]([CH3:12])[C:2](=[O:1])[C:3]=1[CH3:25])[C:14]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[O:15]