丙二酸 → Diisopropyl 2-(2,4,6-Triiodophenoxy)-1,3-propanedioate

HRID 53497

反应方程式

HRID 53497 反应方程式
[I:1][C:2]1[CH:19]=[C:18]([I:20])[CH:17]=[C:16]([I:21])[C:3]=1[O:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])C(OCC)=O.[C:22]([O-])(=O)[CH2:23][C:24]([O-])=O.I[C:30]1C=C(I)C=C(I)C=1O.[C:39](=[O:42])([O-:41])[O-].[K+].[K+]>CCOCC.CN(C)C=O.C(OCC)(=O)C>[I:21][C:16]1[CH:17]=[C:18]([I:20])[CH:19]=[C:2]([I:1])[C:3]=1[O:4][CH:5]([C:11]([O:13][CH:14]([CH3:15])[CH3:30])=[O:12])[C:39]([O:41][CH:23]([CH3:24])[CH3:22])=[O:42]

参与物

8

反应物 4

HCID 9084丙二酸HCID 11430碳酸钾HCID 118622,4,6-三碘苯酚HCID 15343336Diethyl 2-(2,4,6-Triiodophenoxy)-1,3-propanedioate

产物 1

HCID 15343337Diisopropyl 2-(2,4,6-Triiodophenoxy)-1,3-propanedioate

试剂、催化剂与溶剂 3

HCID 3283乙醚溶剂HCID 6228N,N-二甲基甲酰胺溶剂HCID 8857乙酸乙酯溶剂

实验过程

A stirred solution of 18.8 g (0.1 mol) of diisopropyl malonate in 100 ml carbon tetrachloride was cooled in an ice bath and 15.8 g (0.1 mol) bromine was added dropwise over a 90 minute period. The ice bath was removed and the reaction stirred at room temperature for 20 hours. The reaction solution was concentrated in vacuo and the resulting residue distilled to yield 16.1 g (76%) of the bromomalonate I [H. P. Gallus and A. K. Macbeth, J. Chem. Soc., 1937, 1810-12] as a dear colorless liquid; Bp 51°-2° C./0.1 mm Hg. CI/MS: MH+ 26. 1H-NMR (300 MHZ) spectral data was consistent with the desired structure. Using the same procedure as for 2-(2,4,6-triiodophenoxy)-1,3-propanedioic acid, diethyl ester, but substituting methylene chloride for ethyl acetate in the aqueous extraction, 2-(2,4,6-triiodophenoxy)-1,3-propanedioic acid, diisopropyl ester was prepared from 8.6 g (0.03 mol) of malonate I, 107 g (0.03 mol) of 2,4,6-triiodophenol, 4.5 g (0.03 mol) of milled anhydrous potassium carbonate and 30 ml of dimethylformamide in 69% yield as a tan oil; bp >65° C./0.65 mm Hg after chromatography (hexanes to 5% ether in hexanes).

后处理

  1. extractionin the aqueous extraction, 2-(2,4,6-triiodophenoxy)-1,3-propanedioic acid, diisopropyl ester

来源与证据

ORD记录
ord-8d3497e9134b4cc089764820b459e9b8
来源数据集
uspto-grants-1997_04
专利号
US05620677

关联笔记

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