Hydrochloric Acid → ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 345653ノート

反応式

HRID 345653 の反応式
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.[H-].[Na+].[C:14](=O)([O:18]CC)[O:15][CH2:16][CH3:17].Cl>O>[O:10]=[C:9]1[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2][CH2:1][CH:11]1[C:14]([O:15][CH2:16][CH3:17])=[O:18]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 107241-TetraloneHCID 24758Sodium hydride

生成物 1

HCID 251472ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate収率 57.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A suspension of 10 g (0.0684 mole) of α-tetralone, 3.56 g (0.0890 mole) of 60% sodium hydride and 32 g (0.2709 mole) of diethyl carbonate was heated under reflux for 1 hour, then poured into water, adjusted with conc. hydrochloric acid to a pH of 1 to 2, and extracted with ether. The ether layer was washed with water and then dried over magnesium sulfate. After evaporation of the solvent, the crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to obtain 8.6 g of ethyl 1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylate, which was dissolved in tetrahydrofuran (220 ml) and then 1.90 g (0.0475 mole) of 60% sodium hydroxide was added under ice-cooling. After stirring for 30 minutes, 10.0 g (0.0599 mole) of ethyl bromoacetate was added, followed by stirring for 3 hours at room temperature. The reaction mixture was poured into ice-water, extracted with ether, and then the extract was subjected to washing with water, drying and solvent evaporation in a conventional manner. The crude product obtained was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain 9.03 g of the following ethyl 2-ethoxycarbonyl-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetate ##STR13##

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with ether
  4. washThe ether layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

出典と根拠

ORDレコード
ord-91f450b4887e4fb2be85a7895089c52a
出典データセット
uspto-grants-1991_10
特許番号
US05057514

反応ノート

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