Pyridine → HCID 69110769、化合物

HRID 349724ノート

反応式

HRID 349724 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[C:14](=[O:19])[CH2:15][CH:16]([OH:18])[CH:17]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>ClCCl>[C:26]([O:18][CH:16]1[CH2:15][C:14](=[O:19])[C:13]([C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:17]1)(=[O:28])[CH3:27]

参加物

5

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 691095992-(3,4,5-Trimethoxyphenyl)-4-hydroxy-cyclopent-2-en-1-one

生成物 1

HCID 69110769HCID 69110769、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of 2-(3,4,5-trimethoxyphenyl)-4-hydroxy-cyclopent-2-en-1-one (3 gm, 11.36 mmol) in dichloromethane (30 ml) was cooled to 0° C. using ice-salt bath. To the cold solution dry pyridine (1.70 gm, 1.73 ml; 26.0 mmol) was added and stirred at 0° C. for 10 min. To the stirred solution, acetic anhydride (1.63 gm, 1.50 ml, 16.0 mmol) was added dropwise while maintaining the temperature below 0° C. The reaction mixture was stirred at room temperature for 15 h (monitored by TLC) then quenched by adding cold, dilute hydrochloric acid. The organic layer was washed three times with water, 10% sodium bicarbonate solution and finally brine. The organic layer was dried over sodium sulfate and concentrated to dryness under reduced pressure using a rotary evaporator. The crude residue was purified by column chromatography using silica gel (petroleum ether: acetone as eluent) to collect the pure 4-acetoxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.56 gm, 73.47%).

後処理

  1. temperaturewhile maintaining the temperature below 0° C
  2. stirringThe reaction mixture was stirred at room temperature for 15 h (monitored by TLC)
  3. customthen quenched
  4. additionby adding cold
  5. washThe organic layer was washed three times with water, 10% sodium bicarbonate solution and finally brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customa rotary evaporator
  9. customThe crude residue was purified by column chromatography
  10. customto collect the pure 4-acetoxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.56 gm, 73.47%)

出典と根拠

ORDレコード
ord-da71b07023ff466faa38bf466943ef6a
出典データセット
uspto-grants-2007_02
特許番号
US07179937B2

反応ノート

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