三苯基膦 → Methyl 3-(4-{[2'-methyl-4'-(3-(pyridin-2-yl)propoxy)biphenyl-3-yl]methoxy}phenyl)propanoate

HRID 273396

反应方程式

HRID 273396 反应方程式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=3)[CH:9]=2)=[C:4]([CH3:28])[CH:3]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][CH2:36][CH2:37]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:28][C:4]1[CH:3]=[C:2]([O:1][CH2:37][CH2:36][CH2:35][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=2)[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=2)[CH:9]=1

参与物

6

反应物 4

HCID 11776三苯基膦HCID 729222-丙醇吡啶HCID 220568偶氮二甲酸二乙酯HCID 58903183Methyl 3-{4-[(4'-hydroxy-2'-methylbiphenyl-3-yl)methoxy]phenyl}propanoate

产物 1

HCID 58903135Methyl 3-(4-{[2'-methyl-4'-(3-(pyridin-2-yl)propoxy)biphenyl-3-yl]methoxy}phenyl)propanoate收率 56.2%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

A solution of methyl 3-{4-[(4′-hydroxy-2′-methylbiphenyl-3-yl)methoxy]phenyl}propanoate (0.602 g, 1.60 mmol), 3-(pyridin-2-yl)propan-1-ol (0.822 g, 6.00 mmol) and triphenylphosphine (1.57 g, 6.00 mmol) in tetrahydrofuran (20 mL) under ice-cooling was stirred and diethyl azodicarboxylate (40% toluene solution, 2.72 mL, 6.00 mmol) was added. The mixture was warmed to room temperature and stirred for 42 hrs. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane) and preparative HPLC to give the title compound as a yellow viscous oil (0.446 g, yield 56%).

后处理

  1. stirringstirred for 42 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane) and preparative HPLC

来源与证据

ORD记录
ord-15d8bc15785e4575bd3d9f7d1597243e
来源数据集
uspto-grants-2008_11
专利号
US07456218B2

关联笔记

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