三溴化硼 → 5-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

HRID 1616632笔记

反应方程式

HRID 1616632 反应方程式
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([CH3:21])=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19]C)[N:12]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([CH3:21])=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:12]=1

参与物

4

反应物 2

HCID 25134三溴化硼HCID 591677855-[4-(2-Methoxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

产物 1

HCID 684911055-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

Dissolve 5-[4-(2-methoxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester (3.5 g, 11.5 mmol) in CH2Cl2 (50 mL) under nitrogen at RT. Add boron tribromide (1M in CH2Cl2, 29 mL) and stir at RT until the reaction is complete. Quench the mixture into ice/water and extract with CH2Cl2. Dry the combined extracts over Na2SO4 and concentrate. Chromatograph the resulting residue over silica gel (MeOH/CH2Cl2) to allow for isolation of 5-[4-(2-hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester (2.61 g, 78%). MS (ES): (M+1)+ 290.2 m/z.

后处理

  1. customQuench the mixture into ice/water
  2. extractionextract with CH2Cl2
  3. dry with materialDry the combined extracts over Na2SO4
  4. concentrationconcentrate

来源与证据

ORD记录
ord-c2320b2236ad40c68ca630a5de2d187b
来源数据集
uspto-grants-2014_07
专利号
US08765796B2

反应笔记

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