Potassium Carbonate → Diethyl 2-(2,4,6-Triiodophenoxy)-1,3-propanedioate

HRID 53496

反応式

HRID 53496 の反応式
[I:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([I:9])[C:3]=1[OH:10].Br[CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[I:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([I:9])[C:3]=1[O:10][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 69637Diethyl bromomalonate

生成物 1

HCID 15343336Diethyl 2-(2,4,6-Triiodophenoxy)-1,3-propanedioate収率 64%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A stirred mixture of 70.8 g (0.15 mol) of 2,4,6-triiodophenol, 39.0 g (0.15 mol) of diethyl bromomalonate and 20.7 g (0.15 mol) of milled anhydrous potassium carbonate in 200 ml of dry dimethylformamide was heated at 100° C. under argon for 5 hours. The mixture was cooled and concentrated in vacuo. The resulting residue was combined with 300 ml of ice-cold water and the oily product was extracted with ethyl acetate (1×300 ml), 3×100 ml). The combined ethyl acetate extracts were dried (MgSO4) and concentrated in vacuo to a dark oil. The oil was purified by chromatography (eluted by hexanes to 20% diethyl ether in hexanes) to yield 60.2 g (64%) of product as a light cream-colored solid.

後処理

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. extractionthe oily product was extracted with ethyl acetate (1×300 ml), 3×100 ml)
  4. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo to a dark oil
  6. customThe oil was purified by chromatography (eluted by hexanes to 20% diethyl ether in hexanes)

出典と根拠

ORDレコード
ord-171e02d978714c69be10db6b1427fc3a
出典データセット
uspto-grants-1997_04
特許番号
US05620677

関連ノート

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