Acetic Acid → Ethyl 7-[3-(acetyloxy)-5-oxocyclopent-1-EN-1-YL]heptanoate

HRID 67028

反応式

HRID 67028 の反応式
Br[CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1.[C:19]([OH:22])(=[O:21])[CH3:20]>C([O-])(=O)C.[Ag+].CO>[C:19]([O:22][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1)(=[O:21])[CH3:20]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 204655494-Bromo-2-(carbethoxyhexyl)cyclopent-2-en-1-one

生成物 1

HCID 13289791Ethyl 7-[3-(acetyloxy)-5-oxocyclopent-1-EN-1-YL]heptanoate

試薬・触媒・溶媒 2

HCID 11246Silver acetate触媒HCID 887Methanol溶媒

実験手順

A mixture of 51.6 g. (0.137 moles) of crude 4-bromo-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one (Example 1274), 27 g. (0.162 moles) of silver acetate, and 200 ml. of glacial acetic acid is stirred at reflux for 4.5 hours. The mixture is cooled, and solids are removed by filtration. The filtrate is concentrated and extracted with hot hexane. The extract is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over mangesium sulfate, and concentrated to give an oil. The crude product is distilled at reduced pressure to give a liquid, b.p. 152°-163° C. (0.01 mm); λmax.MeOH =223 mμ (10700); νmax.=1745 (ester carbonyl groups), 1725 (ketone carbonyl groups), and 1235 cm-1 (acetoxy group).

後処理

  1. additionA mixture of 51.6 g
  2. temperatureat reflux for 4.5 hours
  3. temperatureThe mixture is cooled
  4. customsolids are removed by filtration
  5. concentrationThe filtrate is concentrated
  6. extractionextracted with hot hexane
  7. washThe extract is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  8. dry with materialdried over mangesium sulfate
  9. concentrationconcentrated
  10. customto give an oil
  11. distillationThe crude product is distilled at reduced pressure
  12. customto give a liquid, b.p. 152°-163° C. (0.01 mm)

出典と根拠

ORDレコード
ord-a1ddf1cc12164e64aed8098986c6f60e
出典データセット
uspto-grants-1982_08
特許番号
US04343949

関連ノート

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