Hydrochloric Acid → HCID 18314014、化合物

HRID 277008ノート

反応式

HRID 277008 の反応式
[H-].[Na+].[C:3](OCC)(=[O:5])[CH3:4].[C:9]([C:12]1[C:13]([CH3:24])=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[S:15][C:16]=1[S:17][CH3:18])(=[O:11])[CH3:10].Cl>O1CCCC1.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1.C(O)C>[CH3:24][C:13]1[C:12]([C:9](=[O:11])[CH2:10][C:3](=[O:5])[CH3:4])=[C:16]([S:17][CH3:18])[S:15][C:14]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 722105ETHYL 4-ACETYL-3-METHYL-5-(METHYLTHIO)THIOPHENE-2-CARBOXYLATE

生成物 1

HCID 18314014HCID 18314014、化合物収率 82.6%

試薬・触媒・溶媒 3

HCID 26541Dibenzo-18-crown-6触媒HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a suspension containing 60% sodium hydride (0.64 g, 15.9 mmol) and ethyl acetate (8.16 g, 92.9 mmol) in tetrahydrofuran (5 ml) were added in turn at room temperature a solution containing ethyl 4-acetyl-3-methyl-5-(methylthio)thiophene-2-carboxylate (2.0 g, 7.7 mmol) and ethanol (0.5 ml) in tetrahydrofuran (10 ml) and a solution containing dibenzo-18-crown-6 ether (0.04 mg) in tetrahydrofuran (5 ml), and the mixture was heated under reflux for 2 hours. The reaction solution was allowed to cool down to room temperature, made acidic by addition of 3N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed (with water and saturated aqueous sodium chloride, in turn), dried (over anhydrous magnesium sulfate) and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=20:1) to afford ethyl 3-methyl-5-methylthio-4-(3-oxobutyryl)thiophene-2-carboxylate (1.91 g, 82%) as yellow -crystals.

後処理

  1. additionwere added in turn at room temperature a solution
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed (with water and saturated aqueous sodium chloride, in turn)
  6. dry with materialdried (over anhydrous magnesium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=20:1)

出典と根拠

ORDレコード
ord-cb6204ce92e745d5b5301edd67a2b977
出典データセット
uspto-grants-2002_03
特許番号
US06355663B1

反応ノート

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