Dimethylformamide → Cyclobutanecarboxylic acid, 3-methylene-, propyl ester

HRID 1412351ノート

反応式

HRID 1412351 の反応式
[CH2:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1.[H-].[Na+].CN(C)C=O.[CH2:16](I)[CH2:17][CH3:18]>C(OCC)(=O)C>[CH2:1]=[C:2]1[CH2:5][CH:4]([C:6]([O:8][CH2:16][CH2:17][CH3:18])=[O:7])[CH2:3]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 274753-Methylenecyclobutanecarboxylic acidHCID 336431-Iodopropane

生成物 1

HCID 45090160Cyclobutanecarboxylic acid, 3-methylene-, propyl ester収率 66%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-methylidenecyclobutanecarboxylic acid (18 g), sodium hydride (6.9 g) and N,N-dimethylformamide (300 mL) was stirred at room temperature for 10 min, propyl iodide (17 mL) was added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogensulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by distillation (45-50° C., 2 mmHg) to give the title compound as a colorless oil (16 g, 66%).

後処理

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. washwashed with 5% aqueous potassium hydrogensulfate solution
  3. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. distillationthe residue was purified by distillation (45-50° C., 2 mmHg)

出典と根拠

ORDレコード
ord-63a560285c2e4203a1afdf1549bc2b56
出典データセット
uspto-grants-2014_12
特許番号
US08921379B2

反応ノート

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