三甲基氯硅烷 → [Methoxy(tetrahydro-4H-pyran-4-ylidene)methoxy](trimethyl)silane

HRID 16583

反应方程式

HRID 16583 反应方程式
C(NC(C)C)(C)C.C([Li])CCC.[O:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]1.[CH3:23][Si:24](Cl)([CH3:26])[CH3:25]>O1CCCC1>[CH3:22][O:21][C:19](=[C:16]1[CH2:17][CH2:18][O:13][CH2:14][CH2:15]1)[O:20][Si:24]([CH3:26])([CH3:25])[CH3:23]

参与物

6

反应物 4

HCID 6397三甲基氯硅烷HCID 7912二异丙胺HCID 2773520四氢吡喃-4-羧酸甲酯HCID 178418339正丁基锂

产物 1

HCID 24897138[Methoxy(tetrahydro-4H-pyran-4-ylidene)methoxy](trimethyl)silane

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

反应条件

温度
-40 °C

实验过程

To a stirred solution of diisopropylamine (1.6 g, 0.016 mol) in tetrahydrofuran (4 mL) was added dropwise n-butyllithium (1.59 M in hexane, 9.2 mL, 0.014 mol) at 0° C. under nitrogen, and stirred for 20 min. Then, the reaction mixture was cooled to −40° C., methyl tetrahydro-2H-pyran-4-carboxylate (1.9 g, 0.013 mol) and trimethylsilyl chloride (2.0 mL, 0.015 mol) in tetrahydrofuran (1 mL) was added, and the resulting mixture was gradually warmed to room temperature over 3 h. The volatile components were removed by evaporation and the residue was filtered through a pad of celite washing with hexane. The filtrate was dried in vacuo to give 2.9 g (quant.) of the title compound as a clear yellow oil.

后处理

  1. temperaturethe resulting mixture was gradually warmed to room temperature over 3 h
  2. customThe volatile components were removed by evaporation
  3. filtrationthe residue was filtered through a pad of celite
  4. washwashing with hexane
  5. customThe filtrate was dried in vacuo

来源与证据

ORD记录
ord-998a23dffdab4159a9def9baf4586bb5
来源数据集
uspto-grants-2010_06
专利号
US07737163B2

关联笔记

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