Dimethylformamide → Butyl 1-(4-iodophenyl)cyclopropane-1-carboxylate

HRID 1274262

Reaktionsgleichung

Reaktionsgleichung von HRID 1274262
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CN([CH:17]=[O:18])C.[C:19](Cl)(=O)[C:20](Cl)=O.[CH2:25](Cl)Cl>>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([O:18][CH2:17][CH2:25][CH2:19][CH3:20])=[O:13])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 217064771-(4-Iodophenyl)cyclopropane-1-carboxylic acid

Produkt 1

HCID 21706508Butyl 1-(4-iodophenyl)cyclopropane-1-carboxylateAusbeute 62 %

Versuchsvorschrift

To a solution of 1-(4-iodophenyl)cyclopropane-1-carboxylic acid (7.98 g, 27 mmol) in methylene chloride (200 mL) containing DMF (0.25 mL) was added dropwise over 30 minutes oxalyl chloride (3.2 mL). The mixture was stirred for 1 hour, and the solvent was removed under reduced pressure. The residue was taken up in THF (100 mL), and potassium t butoxide (1M in THF, 35 mL) was added. After 30 minutes, the mixture was diluted with hexane, washed with water, dried, filtered and evaporated. The solid residue was recrystallized from methanol to give t butyl 1-(4-iodophenyl)cyclopropane-1-carboxylate (5.74 g, 16.6 mmol, 62%).

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. additionpotassium t butoxide (1M in THF, 35 mL) was added
  3. waitAfter 30 minutes
  4. additionthe mixture was diluted with hexane
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe solid residue was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-126a96272b944977819e6671943880eb
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156784

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