Carbon Dioxide → 5-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 370263ノート

反応式

HRID 370263 の反応式
C1O[C:4]2([CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[C:9](Br)[CH:10]=3)[CH2:5]2)OC1.C([Li])(C)(C)C.[C:21](=[O:23])=[O:22].C1C[O:27]CC1>>[C:5]1(=[O:27])[C:6]2[C:11](=[CH:10][C:9]([C:21]([OH:23])=[O:22])=[CH:8][CH:7]=2)[CH2:12][CH2:13][CH2:4]1

参加物

5

反応物 4

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 233778946-Bromo-2-tetralone ethylene ketalHCID 178418306HCID 178418306、化合物

生成物 1

HCID 28184935-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

反応条件

温度
-78 °C

実験手順

6-Bromo-2-tetralone ethylene ketal (2.2 g, 8.15 mmol) was dissolved in anhydrous THF (30 mL), cooled to -78° C. and treated with tert-butyllithium (12.05 mL, 20.4 mmol, 1.7M in pentane) under an atmosphere of nitrogen. After stirring for 30 minutes, anhydrous carbon dioxide gas was passed through the reaction mixture for 20 minutes at -78° C. The suspension was then allowed to warm to ambient temperature. The solution was quenched with water and acidified with 1N HCl, then extracted 2×EtOAc. The organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo to a pale brown oil. The oily residue was applied to a silica flash chromatography column and eluted with 30%-50% EtOAc in hexanes to yield tetralone-6-carboxylic acid, ethylene ketal 1.06 g (55%) of a slowly crystallizing solid. NMR. MS.

後処理

  1. temperatureto warm to ambient temperature
  2. customThe solution was quenched with water
  3. extractionextracted 2×EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo to a pale brown oil
  7. washeluted with 30%-50% EtOAc in hexanes

出典と根拠

ORDレコード
ord-2e532ffd5fd240d0829217706d2b9a4f
出典データセット
uspto-grants-2000_10
特許番号
US06140352

反応ノート

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