三甲基氰硅烷 → 4-[(7,8-Dihydro-8,8-dimethyl-5-trimethylsiloxynaphth-3-yl)ethynyl]benzoic acid

HRID 53391

反应方程式

HRID 53391 反应方程式
[CH3:1][C:2]1([CH3:24])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5](=[O:23])[CH2:4][CH2:3]1.[C:25]([Si:27](C)([CH3:29])[CH3:28])#N>C1COCC1.[I-].[Zn+2].[I-]>[CH3:1][C:2]1([CH3:24])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:21][CH:22]=3)=[CH:7][C:6]=2[C:5]([O:23][Si:27]([CH3:29])([CH3:28])[CH3:25])=[CH:4][CH2:3]1

参与物

5

反应物 2

HCID 82115三甲基氰硅烷HCID 183145934-[(5,6,7,8-Tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoic acid2 次

产物 1

HCID 199623114-[(7,8-Dihydro-8,8-dimethyl-5-trimethylsiloxynaphth-3-yl)ethynyl]benzoic acid

试剂、催化剂与溶剂 2

HCID 9883512zinc(II)iodide催化剂HCID 8028四氢呋喃溶剂2 次

反应条件

温度
25 °C

实验过程

To a cold solution (0° C.) of 50 mg (0.07 mmol) of zinc iodide (dried in vacuo over P2O5 for several hours) in 2 ml of dry THF (flushed with argon) was added a solution of 0.110 g (0.34 mmol) of 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoic acid (Compound 8) in 2 ml of THF followed by 0.14 ml (1.03 mmol) of cyanotrimethylsilane. The resulting mixture was stirred at 25° C. for 12 hours and purified by flash chromatography (silica, 50% EtOAc-hexane) to yield the title compound as a white solid.

后处理

  1. custompurified by flash chromatography (silica, 50% EtOAc-hexane)

来源与证据

ORD记录
ord-35939b1acb954bdebea6354ff1e69bdf
来源数据集
uspto-grants-1997_04
专利号
US05618931

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