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二甲基对苯二胺二盐酸 → t-Butyldimethylsilyloxy-2,6-dipropyl-4-(2-hydroxyethyl)-benzene
参与物
| 角色 | 名称 | HCID | 投料 |
|---|---|---|---|
| 反应物 | 二甲基对苯二胺二盐酸 | HCID 14798 | — |
| 反应物 | 过氧化钠 | HCID 14803 | — |
| 反应物 | Borane;tetrahydrofuran | HCID 2723981 | — |
| 反应物 | t-Butyldimethylsilyloxy-2,6-dipropyl-4-vinyl benzene | HCID 19080390 | — |
| 溶剂 | 四氢呋喃 | HCID 8028 | — |
| 溶剂 | 乙酸乙酯 | HCID 8857 | — |
| 产物 | t-Butyldimethylsilyloxy-2,6-dipropyl-4-(2-hydroxyethyl)-benzene | HCID 19080442 | — |
反应步骤
To a solution of 475 mg (1.48 mmol) of the product of Step B in 3 mL of THF at 0° C. was added 1.6 mL (1.62 mmol) of a 1N borane/THF solution. After 1 hour TLC indicated that the starting material had been consumed. The reaction mixture was quenched with 3 drops of methanol and then 0.70 mL (6.22 mmol) of 30% sodium peroxide and 6.2 mL (6.2 mmol) of 1 N sodium hydroxide were added., After two hours the reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was then dried over sodium sulfate, filtered and concentrated. Flash chromatography (silica gel, hexane/ethyl acetate 4:1) gave 265 mg of the title compound as a clear oil.
来源与证据
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 专利号 | US05565485 |
| 来源数据集 | uspto-grants-1996_10 |
| ORD ID | ord-b53a496cb10045e5b2f6f248bc84daa8 |
| 来源说明 | uspto-grants-1996_10 |