二甲基对苯二胺二盐酸 → t-Butyldimethylsilyloxy-2,6-dipropyl-4-(2-hydroxyethyl)-benzene

HRID 865517

反应方程式

HRID 865517 反应方程式
[Si:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][CH3:17])=[CH:13][C:12]([CH:18]=[CH2:19])=[CH:11][C:10]=1[CH2:20][CH2:21][CH3:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].B.C1C[O:27]CC1.[O-][O-].[Na+].[Na+].[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[Si:1]([O:8][C:9]1[C:10]([CH2:20][CH2:21][CH3:22])=[CH:11][C:12]([CH2:18][CH2:19][OH:27])=[CH:13][C:14]=1[CH2:15][CH2:16][CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参与物

7

反应物 4

HCID 14798二甲基对苯二胺二盐酸HCID 14803过氧化钠HCID 2723981Borane;tetrahydrofuranHCID 19080390t-Butyldimethylsilyloxy-2,6-dipropyl-4-vinyl benzene

产物 1

HCID 19080442t-Butyldimethylsilyloxy-2,6-dipropyl-4-(2-hydroxyethyl)-benzene

试剂、催化剂与溶剂 2

HCID 8028四氢呋喃溶剂HCID 8857乙酸乙酯溶剂

实验过程

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.

后处理

  1. customhad been consumed
  2. customThe reaction mixture was quenched with 3 drops of methanol
  3. washwashed with water and brine
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

来源与证据

ORD记录
ord-b53a496cb10045e5b2f6f248bc84daa8
来源数据集
uspto-grants-1996_10
专利号
US05565485

关联笔记

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