三苯基膦 → Methyl 3-[4-[(3-anilinobenzyl)oxy]phenyl]propanoate

HRID 2422310

反应方程式

HRID 2422310 反应方程式
[NH:1]([C:8]1[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[NH:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[CH2:14][O:15][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参与物

6

反应物 4

HCID 11776三苯基膦HCID 79706对羟基苯丙酸甲酯HCID 12882229(3-(Phenylamino)phenyl)methanolHCID 66777355Diethylazodicarboxylate toluene

产物 1

HCID 57541953Methyl 3-[4-[(3-anilinobenzyl)oxy]phenyl]propanoate收率 50%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
0 °C

实验过程

To a mixture of (3-anilinophenyl)methanol (1.12 g, 5.62 mmol), methyl 3-(4-hydroxyphenyl)propanoate (1.22 g, 6.75 mmol), triphenylphosphine (1.92 g, 7.31 mmol) and tetrahydrofuran (20 mL) was added diethyl azodicarboxylate toluene solution (40%, 3.32 mL) with stirring at 0° C. and the mixture was stirred at room temperature for 14 hrs. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1) to give the title compound (1.01 g, yield 50%) as beige crystals.

后处理

  1. stirringthe mixture was stirred at room temperature for 14 hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1)

来源与证据

ORD记录
ord-91d14e223e39464da398c116911a8c17
来源数据集
uspto-grants-2011_06
专利号
US07960369B2

关联笔记

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