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

HRID 1274262

반응식

HRID 1274262 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-126a96272b944977819e6671943880eb
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06156784

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