2,4,6-Triiodophenol → 2,4,6-Triiodophenyl (2-propyl)pentanoate

HRID 129356

반응식

HRID 129356 반응식
[I:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([I:9])[C:3]=1[OH:10].[CH2:11]([CH:14]([CH2:18][CH2:19]C)[C:15](Cl)=[O:16])[CH2:12][CH3:13].[C:21](=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.C(#N)C>[CH3:21][CH:18]([CH:14]([CH2:11][CH2:12][CH3:13])[C:15]([O:10][C:3]1[C:2]([I:1])=[CH:7][C:6]([I:8])=[CH:5][C:4]=1[I:9])=[O:16])[CH3:19]

참가 물질

6

반응물 3

HCID 118622,4,6-TriiodophenolHCID 762402-Propylvaleryl chlorideHCID 516892Sodium Bicarbonate

생성물 1

HCID 867478922,4,6-Triiodophenyl (2-propyl)pentanoate수율 68%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6342Acetonitrile용매

실험 절차

A mixture of 2,4,6-triiodophenol (2.0 g, 4.24 mmol), 2-propylvaleroyl chloride (2.5 ml, 12.7 mmol, 3 eq) and 4-dimethylaminopyridine (DMAP; 20 mg) in 20 ml of acetonitrile was refluxed under argon overnite. The reaction mixture was cooled and poured into excess aqueous sodium bicarbonate and then extracted with dichloromethane. The dichloromethane extract was dried over magnesium sulfate, filtered, and evaporated to give the crude product (2.42 mmol, 95%) as a pink solid. Recrystallization from ethyl acetate gave 1.75 g (68%) of pure product, mp 99°-101° C.

후처리

  1. temperaturewas refluxed under argon overnite
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with dichloromethane
  4. extractionThe dichloromethane extract
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude product (2.42 mmol, 95%) as a pink solid
  9. customRecrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-8b105aff4e6d46b4b92270d2ff404464
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468466

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