N-三苯甲基-4-哌啶酮 → 4-[4-(2-Oxazolin-2-yl)benzylidene]-1-tritylpiperidine

HRID 129083笔记

反应方程式

HRID 129083 反应方程式
C([Li])CCC.[C:6]([N:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O:32]1[CH2:36][CH2:35][N:34]=[C:33]1[C:37]1[CH:51]=[CH:50][C:40]([CH2:41]P(=O)(OCC)OCC)=[CH:39][CH:38]=1>CCCCCC.O1CCCC1>[O:32]1[CH2:36][CH2:35][N:34]=[C:33]1[C:37]1[CH:38]=[CH:39][C:40]([CH:41]=[C:28]2[CH2:27][CH2:26][N:25]([C:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:30][CH2:29]2)=[CH:50][CH:51]=1

参与物

6

反应物 3

HCID 2748414N-三苯甲基-4-哌啶酮HCID 15231401Diethyl 4-(2-oxazolin-2-yl)benzylphosphonateHCID 178418339正丁基锂

产物 1

HCID 152314024-[4-(2-Oxazolin-2-yl)benzylidene]-1-tritylpiperidine

试剂、催化剂与溶剂 2

HCID 8028四氢呋喃溶剂HCID 8058正己烷溶剂

反应条件

温度
-60 °C

实验过程

6.25 ml of a 1.6M solution of n-butyllithium in hexane followed, after stirring for 20 minutes, by 3.4 g of N-trityl-4-piperidone (prepared from 4-piperidone hydrochloride hydrate and trityl chloride) in 20 ml of tetrahydrofuran are added dropwise at -60° C. to 2.97 g of diethyl 4-(2-oxazolin-2-yl)benzylphosphonate. The mixture is stirred at -60° C. for 25 minutes. The reaction solution is then allowed to warm to ambient temperature and is stirred for a further 1.5 hours at this temperature. The reaction solution is then stirred into 150 ml of ice-water, the mixture is extracted three times with 150 ml of ethyl acetate, and the organic phase is dried and evaporated down. The residue is purified by column chromatography on Silica gel (petroleum ether/ethyl acetate=1:1, v/v). 1.7 g of the title compound of melting point 110°-115° C. are obtained.

后处理

  1. temperatureto warm to ambient temperature
  2. stirringis stirred for a further 1.5 hours at this temperature
  3. extractionthe mixture is extracted three times with 150 ml of ethyl acetate
  4. customthe organic phase is dried
  5. customevaporated down
  6. customThe residue is purified by column chromatography on Silica gel (petroleum ether/ethyl acetate=1:1

来源与证据

ORD记录
ord-049f11e465fb45b2b295bea85faaf69b
来源数据集
uspto-grants-1995_11
专利号
US05466687

反应笔记

加载中…