重氮甲烷 → Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxypentanoate

HRID 463550笔记

反应方程式

HRID 463550 反应方程式
[N+](=[CH2:3])=[N-].[F:4][C:5]([F:31])([F:30])[C:6]1[CH:29]=[CH:28][C:9]([O:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][CH:16]([CH3:25])[CH:17]([OH:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1>CCOCC>[F:4][C:5]([F:30])([F:31])[C:6]1[CH:7]=[CH:8][C:9]([O:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][CH:16]([CH3:25])[CH:17]([O:24][CH3:3])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[CH:28][CH:29]=1

参与物

4

反应物 2

HCID 9550重氮甲烷HCID 12856783Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoate

产物 1

HCID 13488554Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxypentanoate

试剂、催化剂与溶剂 1

HCID 3283乙醚溶剂2 次

实验过程

Diazomethane (2.8 g) in ether (100 ml) is added to ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoate (1.88 g, 3.75 mmol) in ether (5 ml) under N2 and in an ice bath. Small amounts of chromatographic silica gel are added to the mixture in the ice bath until the color disappears. The mixture is then stirred overnight with cooling. The silica gel is removed by filtration and the organic phase is dried and concentrated. The crude product is purified by preparative thin layer chromatography to yield ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxypentanoate (cpd. 1 in Table A). MS m/e 412 (m+).

后处理

  1. temperaturewith cooling
  2. customThe silica gel is removed by filtration
  3. customthe organic phase is dried
  4. concentrationconcentrated
  5. customThe crude product is purified by preparative thin layer chromatography

来源与证据

ORD记录
ord-a5ecd829d2c64042b14c2927f14178f8
来源数据集
uspto-grants-1985_05
专利号
US04520199

反应笔记

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