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

HRID 1005392

反応式

HRID 1005392 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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 (1 M 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%).

後処理

  1. customthe solvent was removed under reduced pressure
  2. additionpotassium t butoxide (1 M 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

出典と根拠

ORDレコード
ord-1bf592bb78da43a3a2dbe5e50cf5cee2
出典データセット
uspto-grants-2000_04
特許番号
US06054470

関連ノート

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