Hydrochloric Acid → Ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate

HRID 504317ノート

反応式

HRID 504317 の反応式
[H-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1.CN(C)C=O.Br[CH2:22][CH2:23]Cl.Cl>CCOC(C)=O>[Cl:3][C:4]1[N:9]=[CH:8][C:7]([C:10]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:23][CH2:22]2)=[CH:6][CH:5]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 15661146Ethyl 2-(6-chloropyridin-3-yl)acetate

生成物 1

HCID 86602273Ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
35 °C

実験手順

Sodium hydride (60% in mineral oil, 0.60 g, 15 mmol) was added to a solution of ethyl (6-chloropyridin-3-yl)acetate (1.0 g, 0.0050 mol) in N,N-dimethylformamide (10 mL, 0.1 mol) at rt under an atmosphere of nitrogen. After 30 minutes, 1-bromo-2-chloro-ethane (0.84 mL, 0.010 mol) was added to the mixture at 0° C. The reaction mixture was stirred at 35° C. for 4 hours and then at room temperature overnight. The mixture was poured into a mixture of ice-water (50 ml) and EtOAc (50 ml) and the resulting mixture was acidified (to pH 2) by slow addition of 6 N HCl. The layers were separated and the organic layer was washed successively with water and brine, dried over MgSO4 and concentrated. The residue was chromatographed by combiflash (ethyl acetate in hexanes: 80%, on silica gel) to afford the desired product. LC/MS: 226.0 and 228.0 (M+H+).

後処理

  1. customat room temperature
  2. customovernight
  3. customThe layers were separated
  4. washthe organic layer was washed successively with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed by combiflash (ethyl acetate in hexanes: 80%, on silica gel)

出典と根拠

ORDレコード
ord-926bb072b96d4e1cb6f33cc5ac04ff81
出典データセット
uspto-grants-2010_08
特許番号
US07776874B2

反応ノート

読み込み中…