Allyl bromide → 2-Chloro-3-(1-propen-3-yl)-4-iodo-6-(1-hydroxyethyl)-pyridine

HRID 1637773

反応式

HRID 1637773 の反応式
[Cl:1][C:2]1[C:7](O)=[C:6]([I:9])[CH:5]=[C:4]([CH:10]([OH:12])[CH3:11])[N:3]=1.[H-].[Na+].[CH2:15](Br)[CH:16]=[CH2:17].C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[C:7]([CH2:17][CH:16]=[CH2:15])=[C:6]([I:9])[CH:5]=[C:4]([CH:10]([OH:12])[CH3:11])[N:3]=1

参加物

6

反応物 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 107092992-Chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine

生成物 1

HCID 187998202-Chloro-3-(1-propen-3-yl)-4-iodo-6-(1-hydroxyethyl)-pyridine収率 93%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2-chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine (3.6 g, 12 mmol) in 24 mL of N,N-dimethylformamide at 0° C. is treated with 480 mg (60% in oil, 12 mmol) of sodium hydride and stirred at room temperature for 1 h. The reaction is treated with 1.14 g (13.2 mmol) of allyl bromide and stirred for 2 h. The mixture is poured into 125 mL of ethyl acetate and washed with 4×50 mL of saturated sodium chloride, 2×25 mL of 50% saturated sodium carbonate and dried over potassium carbonate. The dried organics are concentrated in vacuo, diluted with 20 mL of hexanes, and chilled to -15° C. The solid is filtered to provide 3.61 g (89%) of 2-chloro-3-(1-propen-3-yl)-4-iodo-6-(1-hydroxyethyl)-pyridine.

後処理

  1. stirringstirred for 2 h
  2. washwashed with 4×50 mL of saturated sodium chloride, 2×25 mL of 50% saturated sodium carbonate
  3. dry with materialdried over potassium carbonate
  4. concentrationThe dried organics are concentrated in vacuo
  5. additiondiluted with 20 mL of hexanes
  6. temperaturechilled to -15° C
  7. filtrationThe solid is filtered

出典と根拠

ORDレコード
ord-1504d4b10e5840bea0191d477c57db87
出典データセット
uspto-grants-2000_03
特許番号
US06043248

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