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

HRID 53496

반응식

HRID 53496 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-171e02d978714c69be10db6b1427fc3a
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620677

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