7-(3-Hydroxy-5-oxo-1-cyclopentenyl)-heptanoic acid ethyl ester → 4-Tert-butoxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one

HRID 461261ノート

反応式

HRID 461261 の反応式
BrC1C[C:5](=O)[C:4]([CH2:8]CCCCCC(OCC)=O)=[CH:3]1.[OH:19][CH:20]1[CH2:24][C:23](=[O:25])[C:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:21]1>C(=O)([O-])[O-].[Ag+2].C(O)(C)(C)C>[C:4]([O:19][CH:20]1[CH2:24][C:23](=[O:25])[C:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:21]1)([CH3:8])([CH3:5])[CH3:3]

参加物

5

反応物 2

HCID 98379417-(3-Hydroxy-5-oxo-1-cyclopentenyl)-heptanoic acid ethyl esterHCID 204655494-Bromo-2-(carbethoxyhexyl)cyclopent-2-en-1-one

生成物 1

HCID 233299924-Tert-butoxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 6386tert-Butanol溶媒

実験手順

A stirred mixture of 6.35 g. (20 mmoles) of 4-bromo-2-(carbethoxyhexyl)cyclopent-2-en-1-one (Example 94), 3.01 g. (11 moles) of silver carbonate, and 40 ml. of t-butanol is heated at 70° C. for 17 hours. The mixture is cooled and filtered. After evaporation of t-butanol the residue is treated with aq. sodium chloride and extracted with 3:1 ether-hexane. The extract is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The crude product is purified by chromatography on silica gel to give, in order of elution: the subject compound as an oil; λ maxMeOH. = 219 mμ (8860); ν max. = 1735 (ester carbonyl group), 1725 ketone carbonyl group), and 1365 cm-1 (tert.-butyl group); and 4-hydroxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one also as an oil.

後処理

  1. additionA stirred mixture of 6.35 g
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customAfter evaporation of t-butanol the residue
  5. additionis treated with aq. sodium chloride
  6. extractionextracted with 3:1 ether-hexane
  7. washThe extract is washed with saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe crude product is purified by chromatography on silica gel
  11. customto give, in order of elution

出典と根拠

ORDレコード
ord-73659dede16640cd988d84e9e7c565bb
出典データセット
uspto-grants-1977_12
特許番号
US04061672

反応ノート

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